Tryptophan methyl ester: a proposal of the thermal decomposition mechanism
Abstract Tryptophan (Trp) is a secondary metabolite derived from the shikimate pathway responsible for the synthesis of several alkaloids in some animals and plants. In mammalian metabolism, Trp participates in several biological functions and has a wide application in drug synthesis. In this work,...
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| Autor*in: |
Justino, A. [verfasserIn] |
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| Format: |
E-Artikel |
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| Sprache: |
Englisch |
| Erschienen: |
2021 |
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| Schlagwörter: |
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| Anmerkung: |
© Akadémiai Kiadó, Budapest, Hungary 2021 |
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| Übergeordnetes Werk: |
Enthalten in: Journal of thermal analysis and calorimetry - Dordrecht [u.a.] : Springer Science + Business Media B.V., 1969, 147(2021), 14 vom: 09. Okt., Seite 7741-7748 |
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| Übergeordnetes Werk: |
volume:147 ; year:2021 ; number:14 ; day:09 ; month:10 ; pages:7741-7748 |
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| DOI / URN: |
10.1007/s10973-021-11089-3 |
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| Katalog-ID: |
SPR047374683 |
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| 245 | 1 | 0 | |a Tryptophan methyl ester: a proposal of the thermal decomposition mechanism |
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| 520 | |a Abstract Tryptophan (Trp) is a secondary metabolite derived from the shikimate pathway responsible for the synthesis of several alkaloids in some animals and plants. In mammalian metabolism, Trp participates in several biological functions and has a wide application in drug synthesis. In this work, Trp was used as a starting material for the synthesis of its methyl ester derivative. This compound was characterized by the NMR 1H e 13C, FTIR, TG–DTA, TG–DSC coupled to FTIR, and HPLC/MS techniques. The preliminary tests showed a formation of the tryptophan methyl ester (Z3) as the main product. The thermal behavior of Z3 showed significant changes when compared to its precursor. From the data obtained through thermoanalytical techniques, it was possible to determine a thermal decomposition mechanism for tryptophan methyl ester, as well as isolating and characterizing the intermediary obtained in the first thermal decomposition step, tryptamine. Compound Z3 and intermediate compounds from its thermal decomposition were optimized by molecular modeling, and the theoretical FTIR spectrum of the compounds showed a good correlation with experimental data. | ||
| 650 | 4 | |a Tryptophan methyl ester |7 (dpeaa)DE-He213 | |
| 650 | 4 | |a Thermal behavior |7 (dpeaa)DE-He213 | |
| 650 | 4 | |a Thermal decomposition mechanism |7 (dpeaa)DE-He213 | |
| 650 | 4 | |a Molecular modeling |7 (dpeaa)DE-He213 | |
| 700 | 1 | |a Carvalho, A. C. S. |4 aut | |
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| 700 | 1 | |a Stein, A. L. |4 aut | |
| 700 | 1 | |a Siqueira, A. B. |0 (orcid)0000-0002-4632-4014 |4 aut | |
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10.1007/s10973-021-11089-3 doi (DE-627)SPR047374683 (SPR)s10973-021-11089-3-e DE-627 ger DE-627 rakwb eng Justino, A. verfasserin aut Tryptophan methyl ester: a proposal of the thermal decomposition mechanism 2021 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © Akadémiai Kiadó, Budapest, Hungary 2021 Abstract Tryptophan (Trp) is a secondary metabolite derived from the shikimate pathway responsible for the synthesis of several alkaloids in some animals and plants. In mammalian metabolism, Trp participates in several biological functions and has a wide application in drug synthesis. In this work, Trp was used as a starting material for the synthesis of its methyl ester derivative. This compound was characterized by the NMR 1H e 13C, FTIR, TG–DTA, TG–DSC coupled to FTIR, and HPLC/MS techniques. The preliminary tests showed a formation of the tryptophan methyl ester (Z3) as the main product. The thermal behavior of Z3 showed significant changes when compared to its precursor. From the data obtained through thermoanalytical techniques, it was possible to determine a thermal decomposition mechanism for tryptophan methyl ester, as well as isolating and characterizing the intermediary obtained in the first thermal decomposition step, tryptamine. Compound Z3 and intermediate compounds from its thermal decomposition were optimized by molecular modeling, and the theoretical FTIR spectrum of the compounds showed a good correlation with experimental data. Tryptophan methyl ester (dpeaa)DE-He213 Thermal behavior (dpeaa)DE-He213 Thermal decomposition mechanism (dpeaa)DE-He213 Molecular modeling (dpeaa)DE-He213 Carvalho, A. C. S. aut de Vasconcelos, L. G. aut Gai, B. M. aut Stein, A. L. aut Siqueira, A. B. (orcid)0000-0002-4632-4014 aut Enthalten in Journal of thermal analysis and calorimetry Dordrecht [u.a.] : Springer Science + Business Media B.V., 1969 147(2021), 14 vom: 09. Okt., Seite 7741-7748 (DE-627)315295422 (DE-600)2017304-0 1572-8943 nnns volume:147 year:2021 number:14 day:09 month:10 pages:7741-7748 https://dx.doi.org/10.1007/s10973-021-11089-3 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4328 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 AR 147 2021 14 09 10 7741-7748 |
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10.1007/s10973-021-11089-3 doi (DE-627)SPR047374683 (SPR)s10973-021-11089-3-e DE-627 ger DE-627 rakwb eng Justino, A. verfasserin aut Tryptophan methyl ester: a proposal of the thermal decomposition mechanism 2021 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © Akadémiai Kiadó, Budapest, Hungary 2021 Abstract Tryptophan (Trp) is a secondary metabolite derived from the shikimate pathway responsible for the synthesis of several alkaloids in some animals and plants. In mammalian metabolism, Trp participates in several biological functions and has a wide application in drug synthesis. In this work, Trp was used as a starting material for the synthesis of its methyl ester derivative. This compound was characterized by the NMR 1H e 13C, FTIR, TG–DTA, TG–DSC coupled to FTIR, and HPLC/MS techniques. The preliminary tests showed a formation of the tryptophan methyl ester (Z3) as the main product. The thermal behavior of Z3 showed significant changes when compared to its precursor. From the data obtained through thermoanalytical techniques, it was possible to determine a thermal decomposition mechanism for tryptophan methyl ester, as well as isolating and characterizing the intermediary obtained in the first thermal decomposition step, tryptamine. Compound Z3 and intermediate compounds from its thermal decomposition were optimized by molecular modeling, and the theoretical FTIR spectrum of the compounds showed a good correlation with experimental data. Tryptophan methyl ester (dpeaa)DE-He213 Thermal behavior (dpeaa)DE-He213 Thermal decomposition mechanism (dpeaa)DE-He213 Molecular modeling (dpeaa)DE-He213 Carvalho, A. C. S. aut de Vasconcelos, L. G. aut Gai, B. M. aut Stein, A. L. aut Siqueira, A. B. (orcid)0000-0002-4632-4014 aut Enthalten in Journal of thermal analysis and calorimetry Dordrecht [u.a.] : Springer Science + Business Media B.V., 1969 147(2021), 14 vom: 09. Okt., Seite 7741-7748 (DE-627)315295422 (DE-600)2017304-0 1572-8943 nnns volume:147 year:2021 number:14 day:09 month:10 pages:7741-7748 https://dx.doi.org/10.1007/s10973-021-11089-3 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4328 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 AR 147 2021 14 09 10 7741-7748 |
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10.1007/s10973-021-11089-3 doi (DE-627)SPR047374683 (SPR)s10973-021-11089-3-e DE-627 ger DE-627 rakwb eng Justino, A. verfasserin aut Tryptophan methyl ester: a proposal of the thermal decomposition mechanism 2021 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © Akadémiai Kiadó, Budapest, Hungary 2021 Abstract Tryptophan (Trp) is a secondary metabolite derived from the shikimate pathway responsible for the synthesis of several alkaloids in some animals and plants. In mammalian metabolism, Trp participates in several biological functions and has a wide application in drug synthesis. In this work, Trp was used as a starting material for the synthesis of its methyl ester derivative. This compound was characterized by the NMR 1H e 13C, FTIR, TG–DTA, TG–DSC coupled to FTIR, and HPLC/MS techniques. The preliminary tests showed a formation of the tryptophan methyl ester (Z3) as the main product. The thermal behavior of Z3 showed significant changes when compared to its precursor. From the data obtained through thermoanalytical techniques, it was possible to determine a thermal decomposition mechanism for tryptophan methyl ester, as well as isolating and characterizing the intermediary obtained in the first thermal decomposition step, tryptamine. Compound Z3 and intermediate compounds from its thermal decomposition were optimized by molecular modeling, and the theoretical FTIR spectrum of the compounds showed a good correlation with experimental data. Tryptophan methyl ester (dpeaa)DE-He213 Thermal behavior (dpeaa)DE-He213 Thermal decomposition mechanism (dpeaa)DE-He213 Molecular modeling (dpeaa)DE-He213 Carvalho, A. C. S. aut de Vasconcelos, L. G. aut Gai, B. M. aut Stein, A. L. aut Siqueira, A. B. (orcid)0000-0002-4632-4014 aut Enthalten in Journal of thermal analysis and calorimetry Dordrecht [u.a.] : Springer Science + Business Media B.V., 1969 147(2021), 14 vom: 09. Okt., Seite 7741-7748 (DE-627)315295422 (DE-600)2017304-0 1572-8943 nnns volume:147 year:2021 number:14 day:09 month:10 pages:7741-7748 https://dx.doi.org/10.1007/s10973-021-11089-3 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4328 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 AR 147 2021 14 09 10 7741-7748 |
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10.1007/s10973-021-11089-3 doi (DE-627)SPR047374683 (SPR)s10973-021-11089-3-e DE-627 ger DE-627 rakwb eng Justino, A. verfasserin aut Tryptophan methyl ester: a proposal of the thermal decomposition mechanism 2021 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © Akadémiai Kiadó, Budapest, Hungary 2021 Abstract Tryptophan (Trp) is a secondary metabolite derived from the shikimate pathway responsible for the synthesis of several alkaloids in some animals and plants. In mammalian metabolism, Trp participates in several biological functions and has a wide application in drug synthesis. In this work, Trp was used as a starting material for the synthesis of its methyl ester derivative. This compound was characterized by the NMR 1H e 13C, FTIR, TG–DTA, TG–DSC coupled to FTIR, and HPLC/MS techniques. The preliminary tests showed a formation of the tryptophan methyl ester (Z3) as the main product. The thermal behavior of Z3 showed significant changes when compared to its precursor. From the data obtained through thermoanalytical techniques, it was possible to determine a thermal decomposition mechanism for tryptophan methyl ester, as well as isolating and characterizing the intermediary obtained in the first thermal decomposition step, tryptamine. Compound Z3 and intermediate compounds from its thermal decomposition were optimized by molecular modeling, and the theoretical FTIR spectrum of the compounds showed a good correlation with experimental data. Tryptophan methyl ester (dpeaa)DE-He213 Thermal behavior (dpeaa)DE-He213 Thermal decomposition mechanism (dpeaa)DE-He213 Molecular modeling (dpeaa)DE-He213 Carvalho, A. C. S. aut de Vasconcelos, L. G. aut Gai, B. M. aut Stein, A. L. aut Siqueira, A. B. (orcid)0000-0002-4632-4014 aut Enthalten in Journal of thermal analysis and calorimetry Dordrecht [u.a.] : Springer Science + Business Media B.V., 1969 147(2021), 14 vom: 09. Okt., Seite 7741-7748 (DE-627)315295422 (DE-600)2017304-0 1572-8943 nnns volume:147 year:2021 number:14 day:09 month:10 pages:7741-7748 https://dx.doi.org/10.1007/s10973-021-11089-3 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4328 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 AR 147 2021 14 09 10 7741-7748 |
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10.1007/s10973-021-11089-3 doi (DE-627)SPR047374683 (SPR)s10973-021-11089-3-e DE-627 ger DE-627 rakwb eng Justino, A. verfasserin aut Tryptophan methyl ester: a proposal of the thermal decomposition mechanism 2021 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier © Akadémiai Kiadó, Budapest, Hungary 2021 Abstract Tryptophan (Trp) is a secondary metabolite derived from the shikimate pathway responsible for the synthesis of several alkaloids in some animals and plants. In mammalian metabolism, Trp participates in several biological functions and has a wide application in drug synthesis. In this work, Trp was used as a starting material for the synthesis of its methyl ester derivative. This compound was characterized by the NMR 1H e 13C, FTIR, TG–DTA, TG–DSC coupled to FTIR, and HPLC/MS techniques. The preliminary tests showed a formation of the tryptophan methyl ester (Z3) as the main product. The thermal behavior of Z3 showed significant changes when compared to its precursor. From the data obtained through thermoanalytical techniques, it was possible to determine a thermal decomposition mechanism for tryptophan methyl ester, as well as isolating and characterizing the intermediary obtained in the first thermal decomposition step, tryptamine. Compound Z3 and intermediate compounds from its thermal decomposition were optimized by molecular modeling, and the theoretical FTIR spectrum of the compounds showed a good correlation with experimental data. Tryptophan methyl ester (dpeaa)DE-He213 Thermal behavior (dpeaa)DE-He213 Thermal decomposition mechanism (dpeaa)DE-He213 Molecular modeling (dpeaa)DE-He213 Carvalho, A. C. S. aut de Vasconcelos, L. G. aut Gai, B. M. aut Stein, A. L. aut Siqueira, A. B. (orcid)0000-0002-4632-4014 aut Enthalten in Journal of thermal analysis and calorimetry Dordrecht [u.a.] : Springer Science + Business Media B.V., 1969 147(2021), 14 vom: 09. Okt., Seite 7741-7748 (DE-627)315295422 (DE-600)2017304-0 1572-8943 nnns volume:147 year:2021 number:14 day:09 month:10 pages:7741-7748 https://dx.doi.org/10.1007/s10973-021-11089-3 lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER SSG-OLC-PHA GBV_ILN_11 GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_105 GBV_ILN_110 GBV_ILN_120 GBV_ILN_138 GBV_ILN_150 GBV_ILN_151 GBV_ILN_152 GBV_ILN_161 GBV_ILN_170 GBV_ILN_171 GBV_ILN_187 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_250 GBV_ILN_281 GBV_ILN_285 GBV_ILN_293 GBV_ILN_370 GBV_ILN_602 GBV_ILN_636 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2006 GBV_ILN_2007 GBV_ILN_2008 GBV_ILN_2009 GBV_ILN_2010 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2057 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2088 GBV_ILN_2093 GBV_ILN_2106 GBV_ILN_2107 GBV_ILN_2108 GBV_ILN_2110 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2446 GBV_ILN_2470 GBV_ILN_2472 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_2548 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4046 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4246 GBV_ILN_4249 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4326 GBV_ILN_4328 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4336 GBV_ILN_4338 GBV_ILN_4393 GBV_ILN_4700 AR 147 2021 14 09 10 7741-7748 |
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tryptophan methyl ester: a proposal of the thermal decomposition mechanism |
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Tryptophan methyl ester: a proposal of the thermal decomposition mechanism |
| abstract |
Abstract Tryptophan (Trp) is a secondary metabolite derived from the shikimate pathway responsible for the synthesis of several alkaloids in some animals and plants. In mammalian metabolism, Trp participates in several biological functions and has a wide application in drug synthesis. In this work, Trp was used as a starting material for the synthesis of its methyl ester derivative. This compound was characterized by the NMR 1H e 13C, FTIR, TG–DTA, TG–DSC coupled to FTIR, and HPLC/MS techniques. The preliminary tests showed a formation of the tryptophan methyl ester (Z3) as the main product. The thermal behavior of Z3 showed significant changes when compared to its precursor. From the data obtained through thermoanalytical techniques, it was possible to determine a thermal decomposition mechanism for tryptophan methyl ester, as well as isolating and characterizing the intermediary obtained in the first thermal decomposition step, tryptamine. Compound Z3 and intermediate compounds from its thermal decomposition were optimized by molecular modeling, and the theoretical FTIR spectrum of the compounds showed a good correlation with experimental data. © Akadémiai Kiadó, Budapest, Hungary 2021 |
| abstractGer |
Abstract Tryptophan (Trp) is a secondary metabolite derived from the shikimate pathway responsible for the synthesis of several alkaloids in some animals and plants. In mammalian metabolism, Trp participates in several biological functions and has a wide application in drug synthesis. In this work, Trp was used as a starting material for the synthesis of its methyl ester derivative. This compound was characterized by the NMR 1H e 13C, FTIR, TG–DTA, TG–DSC coupled to FTIR, and HPLC/MS techniques. The preliminary tests showed a formation of the tryptophan methyl ester (Z3) as the main product. The thermal behavior of Z3 showed significant changes when compared to its precursor. From the data obtained through thermoanalytical techniques, it was possible to determine a thermal decomposition mechanism for tryptophan methyl ester, as well as isolating and characterizing the intermediary obtained in the first thermal decomposition step, tryptamine. Compound Z3 and intermediate compounds from its thermal decomposition were optimized by molecular modeling, and the theoretical FTIR spectrum of the compounds showed a good correlation with experimental data. © Akadémiai Kiadó, Budapest, Hungary 2021 |
| abstract_unstemmed |
Abstract Tryptophan (Trp) is a secondary metabolite derived from the shikimate pathway responsible for the synthesis of several alkaloids in some animals and plants. In mammalian metabolism, Trp participates in several biological functions and has a wide application in drug synthesis. In this work, Trp was used as a starting material for the synthesis of its methyl ester derivative. This compound was characterized by the NMR 1H e 13C, FTIR, TG–DTA, TG–DSC coupled to FTIR, and HPLC/MS techniques. The preliminary tests showed a formation of the tryptophan methyl ester (Z3) as the main product. The thermal behavior of Z3 showed significant changes when compared to its precursor. From the data obtained through thermoanalytical techniques, it was possible to determine a thermal decomposition mechanism for tryptophan methyl ester, as well as isolating and characterizing the intermediary obtained in the first thermal decomposition step, tryptamine. Compound Z3 and intermediate compounds from its thermal decomposition were optimized by molecular modeling, and the theoretical FTIR spectrum of the compounds showed a good correlation with experimental data. © Akadémiai Kiadó, Budapest, Hungary 2021 |
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Tryptophan methyl ester: a proposal of the thermal decomposition mechanism |
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https://dx.doi.org/10.1007/s10973-021-11089-3 |
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Carvalho, A. C. S. de Vasconcelos, L. G. Gai, B. M. Stein, A. L. Siqueira, A. B. |
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Carvalho, A. C. S. de Vasconcelos, L. G. Gai, B. M. Stein, A. L. Siqueira, A. B. |
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315295422 |
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| doi_str |
10.1007/s10973-021-11089-3 |
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2024-07-04T02:54:56.184Z |
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| score |
7.3994236 |