Efficient Synthesis of Kinsenoside and Goodyeroside A by a Chemo-Enzymatic Approach

Kinsenoside (1) and goodyeroside A (2), two naturally occurring stereoisomers with diverse biological activities, have been synthesized efficiently by a chemo-enzymatic approach with a total yield of 12.7%. The aglycones, (R)- and (S)-3-hydroxy-γ-butyrolactone, were prepared from D- and L-malic acid...
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Gespeichert in:

Autor*in:	Yang Zhang [verfasserIn] Yihong Xia [verfasserIn] Yongji Lai [verfasserIn] Fang Tang [verfasserIn] Zengwei Luo [verfasserIn] Yongbo Xue [verfasserIn] Guangmin Yao [verfasserIn] Yonghui Zhang [verfasserIn] Jinwen Zhang [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2014

Schlagwörter:	kinsenoside goodyeroside A chemo-enzymatic synthesis glucosidase biocatalysis

Übergeordnetes Werk:	In: Molecules - MDPI AG, 2003, 19(2014), 10, Seite 16950-16958
Übergeordnetes Werk:	volume:19 ; year:2014 ; number:10 ; pages:16950-16958

Links:	Link aufrufen Link aufrufen Link aufrufen Journal toc

DOI / URN:	10.3390/molecules191016950

Katalog-ID:	DOAJ041550722

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allfields	10.3390/molecules191016950 doi (DE-627)DOAJ041550722 (DE-599)DOAJdb23c29ba7ad4618922f66f20a1aa78c DE-627 ger DE-627 rakwb eng QD241-441 Yang Zhang verfasserin aut Efficient Synthesis of Kinsenoside and Goodyeroside A by a Chemo-Enzymatic Approach 2014 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Kinsenoside (1) and goodyeroside A (2), two naturally occurring stereoisomers with diverse biological activities, have been synthesized efficiently by a chemo-enzymatic approach with a total yield of 12.7%. The aglycones, (R)- and (S)-3-hydroxy-γ-butyrolactone, were prepared from D- and L-malic acid by a four-step chemical approach with a yield of 75%, respectively. These butyrolactones were then successfully glycosidated using β-D-glucosidase as a catalyst in a homogeneous organic-water system. Under the optimized enzymatic conditions, the yields of kinsenoside and goodyeroside A in the enzymatic steps both reached 16.8%. kinsenoside goodyeroside A chemo-enzymatic synthesis glucosidase biocatalysis Organic chemistry Yihong Xia verfasserin aut Yongji Lai verfasserin aut Fang Tang verfasserin aut Zengwei Luo verfasserin aut Yongbo Xue verfasserin aut Guangmin Yao verfasserin aut Yonghui Zhang verfasserin aut Jinwen Zhang verfasserin aut In Molecules MDPI AG, 2003 19(2014), 10, Seite 16950-16958 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:19 year:2014 number:10 pages:16950-16958 https://doi.org/10.3390/molecules191016950 kostenfrei https://doaj.org/article/db23c29ba7ad4618922f66f20a1aa78c kostenfrei http://www.mdpi.com/1420-3049/19/10/16950 kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ SSG-OLC-PHA 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 19 2014 10 16950-16958
spelling	10.3390/molecules191016950 doi (DE-627)DOAJ041550722 (DE-599)DOAJdb23c29ba7ad4618922f66f20a1aa78c DE-627 ger DE-627 rakwb eng QD241-441 Yang Zhang verfasserin aut Efficient Synthesis of Kinsenoside and Goodyeroside A by a Chemo-Enzymatic Approach 2014 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Kinsenoside (1) and goodyeroside A (2), two naturally occurring stereoisomers with diverse biological activities, have been synthesized efficiently by a chemo-enzymatic approach with a total yield of 12.7%. The aglycones, (R)- and (S)-3-hydroxy-γ-butyrolactone, were prepared from D- and L-malic acid by a four-step chemical approach with a yield of 75%, respectively. These butyrolactones were then successfully glycosidated using β-D-glucosidase as a catalyst in a homogeneous organic-water system. Under the optimized enzymatic conditions, the yields of kinsenoside and goodyeroside A in the enzymatic steps both reached 16.8%. kinsenoside goodyeroside A chemo-enzymatic synthesis glucosidase biocatalysis Organic chemistry Yihong Xia verfasserin aut Yongji Lai verfasserin aut Fang Tang verfasserin aut Zengwei Luo verfasserin aut Yongbo Xue verfasserin aut Guangmin Yao verfasserin aut Yonghui Zhang verfasserin aut Jinwen Zhang verfasserin aut In Molecules MDPI AG, 2003 19(2014), 10, Seite 16950-16958 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:19 year:2014 number:10 pages:16950-16958 https://doi.org/10.3390/molecules191016950 kostenfrei https://doaj.org/article/db23c29ba7ad4618922f66f20a1aa78c kostenfrei http://www.mdpi.com/1420-3049/19/10/16950 kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ SSG-OLC-PHA 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 19 2014 10 16950-16958
allfields_unstemmed	10.3390/molecules191016950 doi (DE-627)DOAJ041550722 (DE-599)DOAJdb23c29ba7ad4618922f66f20a1aa78c DE-627 ger DE-627 rakwb eng QD241-441 Yang Zhang verfasserin aut Efficient Synthesis of Kinsenoside and Goodyeroside A by a Chemo-Enzymatic Approach 2014 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Kinsenoside (1) and goodyeroside A (2), two naturally occurring stereoisomers with diverse biological activities, have been synthesized efficiently by a chemo-enzymatic approach with a total yield of 12.7%. The aglycones, (R)- and (S)-3-hydroxy-γ-butyrolactone, were prepared from D- and L-malic acid by a four-step chemical approach with a yield of 75%, respectively. These butyrolactones were then successfully glycosidated using β-D-glucosidase as a catalyst in a homogeneous organic-water system. Under the optimized enzymatic conditions, the yields of kinsenoside and goodyeroside A in the enzymatic steps both reached 16.8%. kinsenoside goodyeroside A chemo-enzymatic synthesis glucosidase biocatalysis Organic chemistry Yihong Xia verfasserin aut Yongji Lai verfasserin aut Fang Tang verfasserin aut Zengwei Luo verfasserin aut Yongbo Xue verfasserin aut Guangmin Yao verfasserin aut Yonghui Zhang verfasserin aut Jinwen Zhang verfasserin aut In Molecules MDPI AG, 2003 19(2014), 10, Seite 16950-16958 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:19 year:2014 number:10 pages:16950-16958 https://doi.org/10.3390/molecules191016950 kostenfrei https://doaj.org/article/db23c29ba7ad4618922f66f20a1aa78c kostenfrei http://www.mdpi.com/1420-3049/19/10/16950 kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ SSG-OLC-PHA 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 19 2014 10 16950-16958
allfieldsGer	10.3390/molecules191016950 doi (DE-627)DOAJ041550722 (DE-599)DOAJdb23c29ba7ad4618922f66f20a1aa78c DE-627 ger DE-627 rakwb eng QD241-441 Yang Zhang verfasserin aut Efficient Synthesis of Kinsenoside and Goodyeroside A by a Chemo-Enzymatic Approach 2014 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Kinsenoside (1) and goodyeroside A (2), two naturally occurring stereoisomers with diverse biological activities, have been synthesized efficiently by a chemo-enzymatic approach with a total yield of 12.7%. The aglycones, (R)- and (S)-3-hydroxy-γ-butyrolactone, were prepared from D- and L-malic acid by a four-step chemical approach with a yield of 75%, respectively. These butyrolactones were then successfully glycosidated using β-D-glucosidase as a catalyst in a homogeneous organic-water system. Under the optimized enzymatic conditions, the yields of kinsenoside and goodyeroside A in the enzymatic steps both reached 16.8%. kinsenoside goodyeroside A chemo-enzymatic synthesis glucosidase biocatalysis Organic chemistry Yihong Xia verfasserin aut Yongji Lai verfasserin aut Fang Tang verfasserin aut Zengwei Luo verfasserin aut Yongbo Xue verfasserin aut Guangmin Yao verfasserin aut Yonghui Zhang verfasserin aut Jinwen Zhang verfasserin aut In Molecules MDPI AG, 2003 19(2014), 10, Seite 16950-16958 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:19 year:2014 number:10 pages:16950-16958 https://doi.org/10.3390/molecules191016950 kostenfrei https://doaj.org/article/db23c29ba7ad4618922f66f20a1aa78c kostenfrei http://www.mdpi.com/1420-3049/19/10/16950 kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ SSG-OLC-PHA 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 19 2014 10 16950-16958
allfieldsSound	10.3390/molecules191016950 doi (DE-627)DOAJ041550722 (DE-599)DOAJdb23c29ba7ad4618922f66f20a1aa78c DE-627 ger DE-627 rakwb eng QD241-441 Yang Zhang verfasserin aut Efficient Synthesis of Kinsenoside and Goodyeroside A by a Chemo-Enzymatic Approach 2014 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Kinsenoside (1) and goodyeroside A (2), two naturally occurring stereoisomers with diverse biological activities, have been synthesized efficiently by a chemo-enzymatic approach with a total yield of 12.7%. The aglycones, (R)- and (S)-3-hydroxy-γ-butyrolactone, were prepared from D- and L-malic acid by a four-step chemical approach with a yield of 75%, respectively. These butyrolactones were then successfully glycosidated using β-D-glucosidase as a catalyst in a homogeneous organic-water system. Under the optimized enzymatic conditions, the yields of kinsenoside and goodyeroside A in the enzymatic steps both reached 16.8%. kinsenoside goodyeroside A chemo-enzymatic synthesis glucosidase biocatalysis Organic chemistry Yihong Xia verfasserin aut Yongji Lai verfasserin aut Fang Tang verfasserin aut Zengwei Luo verfasserin aut Yongbo Xue verfasserin aut Guangmin Yao verfasserin aut Yonghui Zhang verfasserin aut Jinwen Zhang verfasserin aut In Molecules MDPI AG, 2003 19(2014), 10, Seite 16950-16958 (DE-627)311313132 (DE-600)2008644-1 14203049 nnns volume:19 year:2014 number:10 pages:16950-16958 https://doi.org/10.3390/molecules191016950 kostenfrei https://doaj.org/article/db23c29ba7ad4618922f66f20a1aa78c kostenfrei http://www.mdpi.com/1420-3049/19/10/16950 kostenfrei https://doaj.org/toc/1420-3049 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ SSG-OLC-PHA 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 19 2014 10 16950-16958
language	English
source	In Molecules 19(2014), 10, Seite 16950-16958 volume:19 year:2014 number:10 pages:16950-16958
sourceStr	In Molecules 19(2014), 10, Seite 16950-16958 volume:19 year:2014 number:10 pages:16950-16958
format_phy_str_mv	Article
institution	findex.gbv.de
topic_facet	kinsenoside goodyeroside A chemo-enzymatic synthesis glucosidase biocatalysis Organic chemistry
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container_title	Molecules
authorswithroles_txt_mv	Yang Zhang @@aut@@ Yihong Xia @@aut@@ Yongji Lai @@aut@@ Fang Tang @@aut@@ Zengwei Luo @@aut@@ Yongbo Xue @@aut@@ Guangmin Yao @@aut@@ Yonghui Zhang @@aut@@ Jinwen Zhang @@aut@@
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callnumber-first	Q - Science
author	Yang Zhang
spellingShingle	Yang Zhang misc QD241-441 misc kinsenoside misc goodyeroside A misc chemo-enzymatic synthesis misc glucosidase misc biocatalysis misc Organic chemistry Efficient Synthesis of Kinsenoside and Goodyeroside A by a Chemo-Enzymatic Approach
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topic_title	QD241-441 Efficient Synthesis of Kinsenoside and Goodyeroside A by a Chemo-Enzymatic Approach kinsenoside goodyeroside A chemo-enzymatic synthesis glucosidase biocatalysis
topic	misc QD241-441 misc kinsenoside misc goodyeroside A misc chemo-enzymatic synthesis misc glucosidase misc biocatalysis misc Organic chemistry
topic_unstemmed	misc QD241-441 misc kinsenoside misc goodyeroside A misc chemo-enzymatic synthesis misc glucosidase misc biocatalysis misc Organic chemistry
topic_browse	misc QD241-441 misc kinsenoside misc goodyeroside A misc chemo-enzymatic synthesis misc glucosidase misc biocatalysis misc Organic chemistry
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title	Efficient Synthesis of Kinsenoside and Goodyeroside A by a Chemo-Enzymatic Approach
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title_full	Efficient Synthesis of Kinsenoside and Goodyeroside A by a Chemo-Enzymatic Approach
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author_browse	Yang Zhang Yihong Xia Yongji Lai Fang Tang Zengwei Luo Yongbo Xue Guangmin Yao Yonghui Zhang Jinwen Zhang
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title_sort	efficient synthesis of kinsenoside and goodyeroside a by a chemo-enzymatic approach
callnumber	QD241-441
title_auth	Efficient Synthesis of Kinsenoside and Goodyeroside A by a Chemo-Enzymatic Approach
abstract	Kinsenoside (1) and goodyeroside A (2), two naturally occurring stereoisomers with diverse biological activities, have been synthesized efficiently by a chemo-enzymatic approach with a total yield of 12.7%. The aglycones, (R)- and (S)-3-hydroxy-γ-butyrolactone, were prepared from D- and L-malic acid by a four-step chemical approach with a yield of 75%, respectively. These butyrolactones were then successfully glycosidated using β-D-glucosidase as a catalyst in a homogeneous organic-water system. Under the optimized enzymatic conditions, the yields of kinsenoside and goodyeroside A in the enzymatic steps both reached 16.8%.
abstractGer	Kinsenoside (1) and goodyeroside A (2), two naturally occurring stereoisomers with diverse biological activities, have been synthesized efficiently by a chemo-enzymatic approach with a total yield of 12.7%. The aglycones, (R)- and (S)-3-hydroxy-γ-butyrolactone, were prepared from D- and L-malic acid by a four-step chemical approach with a yield of 75%, respectively. These butyrolactones were then successfully glycosidated using β-D-glucosidase as a catalyst in a homogeneous organic-water system. Under the optimized enzymatic conditions, the yields of kinsenoside and goodyeroside A in the enzymatic steps both reached 16.8%.
abstract_unstemmed	Kinsenoside (1) and goodyeroside A (2), two naturally occurring stereoisomers with diverse biological activities, have been synthesized efficiently by a chemo-enzymatic approach with a total yield of 12.7%. The aglycones, (R)- and (S)-3-hydroxy-γ-butyrolactone, were prepared from D- and L-malic acid by a four-step chemical approach with a yield of 75%, respectively. These butyrolactones were then successfully glycosidated using β-D-glucosidase as a catalyst in a homogeneous organic-water system. Under the optimized enzymatic conditions, the yields of kinsenoside and goodyeroside A in the enzymatic steps both reached 16.8%.
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container_issue	10
title_short	Efficient Synthesis of Kinsenoside and Goodyeroside A by a Chemo-Enzymatic Approach
url	https://doi.org/10.3390/molecules191016950 https://doaj.org/article/db23c29ba7ad4618922f66f20a1aa78c http://www.mdpi.com/1420-3049/19/10/16950 https://doaj.org/toc/1420-3049
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up_date	2024-07-03T20:51:18.637Z
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Efficient Synthesis of Kinsenoside and Goodyeroside A by a Chemo-Enzymatic Approach

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