Thiocholine-Mediated One-Pot Peptide Ligation and Desulfurization

Thiol catalysts are essential in native chemical ligation (NCL) to increase the reaction efficiency. In this paper, we report the use of thiocholine in chemical protein synthesis, including NCL-based peptide ligation and metal-free desulfurization. Evaluation of thiocholine peptide thioester in term...
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Autor*in:	Sae Suzuki [verfasserIn] Yuya Nakajima [verfasserIn] Naoki Kamo [verfasserIn] Akihisa Osakabe [verfasserIn] Akimitsu Okamoto [verfasserIn] Gosuke Hayashi [verfasserIn] Hiroshi Murakami [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2023

Schlagwörter:	chemical protein synthesis native chemical ligation desulfurization one-pot synthesis

Übergeordnetes Werk:	In: Molecules - MDPI AG, 2003, 28(2023), 9, p 3655
Übergeordnetes Werk:	volume:28 ; year:2023 ; number:9, p 3655

Links:	Link aufrufen Link aufrufen Link aufrufen Journal toc

DOI / URN:	10.3390/molecules28093655

Katalog-ID:	DOAJ090352289

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520			\|a Thiol catalysts are essential in native chemical ligation (NCL) to increase the reaction efficiency. In this paper, we report the use of thiocholine in chemical protein synthesis, including NCL-based peptide ligation and metal-free desulfurization. Evaluation of thiocholine peptide thioester in terms of NCL and hydrolysis kinetics revealed its practical utility, which was comparable to that of other alkyl thioesters. Importantly, thiocholine showed better reactivity as a thiol additive in desulfurization, which is often used in chemical protein synthesis to convert Cys residues to more abundant Ala residues. Finally, we achieved chemical synthesis of two differently methylated histone H3 proteins via one-pot NCL and desulfurization with thiocholine.
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allfields	10.3390/molecules28093655 doi (DE-627)DOAJ090352289 (DE-599)DOAJa824ab86b6404c34818ed9b9438ba516 DE-627 ger DE-627 rakwb eng QD241-441 Sae Suzuki verfasserin aut Thiocholine-Mediated One-Pot Peptide Ligation and Desulfurization 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Thiol catalysts are essential in native chemical ligation (NCL) to increase the reaction efficiency. In this paper, we report the use of thiocholine in chemical protein synthesis, including NCL-based peptide ligation and metal-free desulfurization. Evaluation of thiocholine peptide thioester in terms of NCL and hydrolysis kinetics revealed its practical utility, which was comparable to that of other alkyl thioesters. Importantly, thiocholine showed better reactivity as a thiol additive in desulfurization, which is often used in chemical protein synthesis to convert Cys residues to more abundant Ala residues. Finally, we achieved chemical synthesis of two differently methylated histone H3 proteins via one-pot NCL and desulfurization with thiocholine. chemical protein synthesis native chemical ligation desulfurization one-pot synthesis Organic chemistry Yuya Nakajima verfasserin aut Naoki Kamo verfasserin aut Akihisa Osakabe verfasserin aut Akimitsu Okamoto verfasserin aut Gosuke Hayashi verfasserin aut Hiroshi Murakami verfasserin aut In Molecules MDPI AG, 2003 28(2023), 9, p 3655 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:28 year:2023 number:9, p 3655 https://doi.org/10.3390/molecules28093655 kostenfrei https://doaj.org/article/a824ab86b6404c34818ed9b9438ba516 kostenfrei https://www.mdpi.com/1420-3049/28/9/3655 kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 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_4338 GBV_ILN_4367 GBV_ILN_4700 AR 28 2023 9, p 3655
spelling	10.3390/molecules28093655 doi (DE-627)DOAJ090352289 (DE-599)DOAJa824ab86b6404c34818ed9b9438ba516 DE-627 ger DE-627 rakwb eng QD241-441 Sae Suzuki verfasserin aut Thiocholine-Mediated One-Pot Peptide Ligation and Desulfurization 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Thiol catalysts are essential in native chemical ligation (NCL) to increase the reaction efficiency. In this paper, we report the use of thiocholine in chemical protein synthesis, including NCL-based peptide ligation and metal-free desulfurization. Evaluation of thiocholine peptide thioester in terms of NCL and hydrolysis kinetics revealed its practical utility, which was comparable to that of other alkyl thioesters. Importantly, thiocholine showed better reactivity as a thiol additive in desulfurization, which is often used in chemical protein synthesis to convert Cys residues to more abundant Ala residues. Finally, we achieved chemical synthesis of two differently methylated histone H3 proteins via one-pot NCL and desulfurization with thiocholine. chemical protein synthesis native chemical ligation desulfurization one-pot synthesis Organic chemistry Yuya Nakajima verfasserin aut Naoki Kamo verfasserin aut Akihisa Osakabe verfasserin aut Akimitsu Okamoto verfasserin aut Gosuke Hayashi verfasserin aut Hiroshi Murakami verfasserin aut In Molecules MDPI AG, 2003 28(2023), 9, p 3655 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:28 year:2023 number:9, p 3655 https://doi.org/10.3390/molecules28093655 kostenfrei https://doaj.org/article/a824ab86b6404c34818ed9b9438ba516 kostenfrei https://www.mdpi.com/1420-3049/28/9/3655 kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 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_4338 GBV_ILN_4367 GBV_ILN_4700 AR 28 2023 9, p 3655
allfields_unstemmed	10.3390/molecules28093655 doi (DE-627)DOAJ090352289 (DE-599)DOAJa824ab86b6404c34818ed9b9438ba516 DE-627 ger DE-627 rakwb eng QD241-441 Sae Suzuki verfasserin aut Thiocholine-Mediated One-Pot Peptide Ligation and Desulfurization 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Thiol catalysts are essential in native chemical ligation (NCL) to increase the reaction efficiency. In this paper, we report the use of thiocholine in chemical protein synthesis, including NCL-based peptide ligation and metal-free desulfurization. Evaluation of thiocholine peptide thioester in terms of NCL and hydrolysis kinetics revealed its practical utility, which was comparable to that of other alkyl thioesters. Importantly, thiocholine showed better reactivity as a thiol additive in desulfurization, which is often used in chemical protein synthesis to convert Cys residues to more abundant Ala residues. Finally, we achieved chemical synthesis of two differently methylated histone H3 proteins via one-pot NCL and desulfurization with thiocholine. chemical protein synthesis native chemical ligation desulfurization one-pot synthesis Organic chemistry Yuya Nakajima verfasserin aut Naoki Kamo verfasserin aut Akihisa Osakabe verfasserin aut Akimitsu Okamoto verfasserin aut Gosuke Hayashi verfasserin aut Hiroshi Murakami verfasserin aut In Molecules MDPI AG, 2003 28(2023), 9, p 3655 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:28 year:2023 number:9, p 3655 https://doi.org/10.3390/molecules28093655 kostenfrei https://doaj.org/article/a824ab86b6404c34818ed9b9438ba516 kostenfrei https://www.mdpi.com/1420-3049/28/9/3655 kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 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_4338 GBV_ILN_4367 GBV_ILN_4700 AR 28 2023 9, p 3655
allfieldsGer	10.3390/molecules28093655 doi (DE-627)DOAJ090352289 (DE-599)DOAJa824ab86b6404c34818ed9b9438ba516 DE-627 ger DE-627 rakwb eng QD241-441 Sae Suzuki verfasserin aut Thiocholine-Mediated One-Pot Peptide Ligation and Desulfurization 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Thiol catalysts are essential in native chemical ligation (NCL) to increase the reaction efficiency. In this paper, we report the use of thiocholine in chemical protein synthesis, including NCL-based peptide ligation and metal-free desulfurization. Evaluation of thiocholine peptide thioester in terms of NCL and hydrolysis kinetics revealed its practical utility, which was comparable to that of other alkyl thioesters. Importantly, thiocholine showed better reactivity as a thiol additive in desulfurization, which is often used in chemical protein synthesis to convert Cys residues to more abundant Ala residues. Finally, we achieved chemical synthesis of two differently methylated histone H3 proteins via one-pot NCL and desulfurization with thiocholine. chemical protein synthesis native chemical ligation desulfurization one-pot synthesis Organic chemistry Yuya Nakajima verfasserin aut Naoki Kamo verfasserin aut Akihisa Osakabe verfasserin aut Akimitsu Okamoto verfasserin aut Gosuke Hayashi verfasserin aut Hiroshi Murakami verfasserin aut In Molecules MDPI AG, 2003 28(2023), 9, p 3655 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:28 year:2023 number:9, p 3655 https://doi.org/10.3390/molecules28093655 kostenfrei https://doaj.org/article/a824ab86b6404c34818ed9b9438ba516 kostenfrei https://www.mdpi.com/1420-3049/28/9/3655 kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 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_4338 GBV_ILN_4367 GBV_ILN_4700 AR 28 2023 9, p 3655
allfieldsSound	10.3390/molecules28093655 doi (DE-627)DOAJ090352289 (DE-599)DOAJa824ab86b6404c34818ed9b9438ba516 DE-627 ger DE-627 rakwb eng QD241-441 Sae Suzuki verfasserin aut Thiocholine-Mediated One-Pot Peptide Ligation and Desulfurization 2023 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Thiol catalysts are essential in native chemical ligation (NCL) to increase the reaction efficiency. In this paper, we report the use of thiocholine in chemical protein synthesis, including NCL-based peptide ligation and metal-free desulfurization. Evaluation of thiocholine peptide thioester in terms of NCL and hydrolysis kinetics revealed its practical utility, which was comparable to that of other alkyl thioesters. Importantly, thiocholine showed better reactivity as a thiol additive in desulfurization, which is often used in chemical protein synthesis to convert Cys residues to more abundant Ala residues. Finally, we achieved chemical synthesis of two differently methylated histone H3 proteins via one-pot NCL and desulfurization with thiocholine. chemical protein synthesis native chemical ligation desulfurization one-pot synthesis Organic chemistry Yuya Nakajima verfasserin aut Naoki Kamo verfasserin aut Akihisa Osakabe verfasserin aut Akimitsu Okamoto verfasserin aut Gosuke Hayashi verfasserin aut Hiroshi Murakami verfasserin aut In Molecules MDPI AG, 2003 28(2023), 9, p 3655 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:28 year:2023 number:9, p 3655 https://doi.org/10.3390/molecules28093655 kostenfrei https://doaj.org/article/a824ab86b6404c34818ed9b9438ba516 kostenfrei https://www.mdpi.com/1420-3049/28/9/3655 kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 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_4338 GBV_ILN_4367 GBV_ILN_4700 AR 28 2023 9, p 3655
language	English
source	In Molecules 28(2023), 9, p 3655 volume:28 year:2023 number:9, p 3655
sourceStr	In Molecules 28(2023), 9, p 3655 volume:28 year:2023 number:9, p 3655
format_phy_str_mv	Article
institution	findex.gbv.de
topic_facet	chemical protein synthesis native chemical ligation desulfurization one-pot synthesis Organic chemistry
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container_title	Molecules
authorswithroles_txt_mv	Sae Suzuki @@aut@@ Yuya Nakajima @@aut@@ Naoki Kamo @@aut@@ Akihisa Osakabe @@aut@@ Akimitsu Okamoto @@aut@@ Gosuke Hayashi @@aut@@ Hiroshi Murakami @@aut@@
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callnumber-first	Q - Science
author	Sae Suzuki
spellingShingle	Sae Suzuki misc QD241-441 misc chemical protein synthesis misc native chemical ligation misc desulfurization misc one-pot synthesis misc Organic chemistry Thiocholine-Mediated One-Pot Peptide Ligation and Desulfurization
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topic_title	QD241-441 Thiocholine-Mediated One-Pot Peptide Ligation and Desulfurization chemical protein synthesis native chemical ligation desulfurization one-pot synthesis
topic	misc QD241-441 misc chemical protein synthesis misc native chemical ligation misc desulfurization misc one-pot synthesis misc Organic chemistry
topic_unstemmed	misc QD241-441 misc chemical protein synthesis misc native chemical ligation misc desulfurization misc one-pot synthesis misc Organic chemistry
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title	Thiocholine-Mediated One-Pot Peptide Ligation and Desulfurization
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title_sort	thiocholine-mediated one-pot peptide ligation and desulfurization
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title_auth	Thiocholine-Mediated One-Pot Peptide Ligation and Desulfurization
abstract	Thiol catalysts are essential in native chemical ligation (NCL) to increase the reaction efficiency. In this paper, we report the use of thiocholine in chemical protein synthesis, including NCL-based peptide ligation and metal-free desulfurization. Evaluation of thiocholine peptide thioester in terms of NCL and hydrolysis kinetics revealed its practical utility, which was comparable to that of other alkyl thioesters. Importantly, thiocholine showed better reactivity as a thiol additive in desulfurization, which is often used in chemical protein synthesis to convert Cys residues to more abundant Ala residues. Finally, we achieved chemical synthesis of two differently methylated histone H3 proteins via one-pot NCL and desulfurization with thiocholine.
abstractGer	Thiol catalysts are essential in native chemical ligation (NCL) to increase the reaction efficiency. In this paper, we report the use of thiocholine in chemical protein synthesis, including NCL-based peptide ligation and metal-free desulfurization. Evaluation of thiocholine peptide thioester in terms of NCL and hydrolysis kinetics revealed its practical utility, which was comparable to that of other alkyl thioesters. Importantly, thiocholine showed better reactivity as a thiol additive in desulfurization, which is often used in chemical protein synthesis to convert Cys residues to more abundant Ala residues. Finally, we achieved chemical synthesis of two differently methylated histone H3 proteins via one-pot NCL and desulfurization with thiocholine.
abstract_unstemmed	Thiol catalysts are essential in native chemical ligation (NCL) to increase the reaction efficiency. In this paper, we report the use of thiocholine in chemical protein synthesis, including NCL-based peptide ligation and metal-free desulfurization. Evaluation of thiocholine peptide thioester in terms of NCL and hydrolysis kinetics revealed its practical utility, which was comparable to that of other alkyl thioesters. Importantly, thiocholine showed better reactivity as a thiol additive in desulfurization, which is often used in chemical protein synthesis to convert Cys residues to more abundant Ala residues. Finally, we achieved chemical synthesis of two differently methylated histone H3 proteins via one-pot NCL and desulfurization with thiocholine.
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title_short	Thiocholine-Mediated One-Pot Peptide Ligation and Desulfurization
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Thiocholine-Mediated One-Pot Peptide Ligation and Desulfurization

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Vorhandene Bände

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