HOAt.DCHA as co-coupling agent in the synthesis of peptides employing Fmoc-amino acid chlorides as coupling agents: Application to the synthesis of β-casomorphin

Vommina V Sureshbabu; Gundala Chennakrishnareddy

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HOAt.DCHA as co-coupling agent in the synthesis of peptides employing Fmoc-amino acid chlorides as coupling agents: Application to the synthesis of β-casomorphin

机译：以Fmoc-氨基酸氯化物为偶联剂的HOAt.DCHA在肽合成中的共偶联剂：在β-酪蛋白的合成中的应用

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A simple, efficient and racemization free method for the synthesis of peptides employing Fmoc-amino acid chlorides mediated by HOAt.DCHA as a co-coupling agent has been described. This protocol is successfully employed in the synthesis of the pentapeptide H-Pro-Gly-Val-Gly-Val-OH (PGVGV), and β-casomorphin (H-Tyr-Pro-Phe-Pro-Gly-OH) in 85 and 80% yields, respectively.

机译：已经描述了一种简单，有效且无外消旋的方法来合成肽，该方法采用由HOAt.DCHA介导的Fmoc-氨基酸氯化物作为助偶联剂。该方案已成功用于在85和90℃下合成五肽H-Pro-Gly-Val-Gly-Val-OH（PGVGV）和β-casomorphin（H-Tyr-Pro-Phe-Pro-Gly-OH）产率分别为80％。

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《Indian Journal of Chemistry, Section B. Organic Including Medicinal》 |2009年第7期|共8页
作者
Vommina V Sureshbabu; Gundala Chennakrishnareddy;
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正文语种 eng
中图分类化学;
关键词
Amino acid chlorides; 1-hydroxy-7-azabenzotriazole; co-coupling agent; non Schotten-Baumann condition; racemization free coupling;

机译：氨基酸氯化物;1-羟基-7-氮杂苯并三唑;共偶联剂;非肖特-鲍曼条件;消旋自由偶联;

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1. HOAt.DCHA as co-coupling agent in the synthesis of peptides employing Fmoc-amino acid chlorides as coupling agents: Application to the synthesis of β-casomorphin [J] . Vommina V Sureshbabu, Gundala Chennakrishnareddy Indian Journal of Chemistry, Section B. Organic Including Medicinal . 2009,第7期

机译：以Fmoc-氨基酸氯化物为偶联剂的HOAt.DCHA在肽合成中的共偶联剂：在β-酪蛋白的合成中的应用
2. Synthesis of beta-casomorphin employing Fmoc-amino acid chlorides and t-butyldimethylsilyloxy benzotriazole (TBDMS-OBt) [J] . Subramanyam J Tantry, Raveendra I Mathad, Vommina V Suresh Babu Indian Journal of Chemistry, Section B. Organic Including Medicinal . 2003,第9期

机译：使用Fmoc-氨基酸氯化物和叔丁基二甲基甲硅烷氧基苯并三唑（TBDMS-OBt）合成β-casomorphin
3. A rapid and efficient synthesis of beta-casomorphin employing Boc-amino acids and 9-fluofenylmethyl chloroformate as a coupling agent [J] . V V Suresh Babu, S J Tantry Indian Journal of Chemistry, Section B. Organic Including Medicinal . 2004,第12期

机译：使用Boc氨基酸和9-氟烯基氯甲酸甲酯作为偶联剂快速有效地合成β-casomorphin
4. Synthesis and Application of Amphoteric Polymer Dimethyl Diallyl Ammonium Chloride/ Acrylic Acid as Less-chrome Tanning Agent [C] . MA Jianzhong, LI Yun, GAO Dangge, Proceedings of the 12th international wool research conference.;vol. 2. . 2010

机译：两性聚合物二甲基氯化二甲基烯丙基氯化铵/丙烯酸作为少铬鞣剂的合成及应用
5. 1. Reduction of Tertiary Benzamides to Benzaldehydes by an in situ-Generated Schwartz Reagent (Cp2 Zirconium (Hydrogen)Chloride); Formal Synthesis of Lysergic Acid. 2. Ru-Catalyzed Amide-Directed Aryl Carbon-Hydrogen, Carbon-Nitrogen and Carbon-Oxygen Bond Functionalizations: C-B Formation, Carbon-Carbon Suzuki Cross Coupling and Hydrodemethoxylation [D] . Zhao, Yigang 2011

机译：1.通过原位生成的Schwartz试剂（Cp2氯化锆（氢）氯化物）将叔苄酰胺还原为苯甲醛；麦角酸的正式合成。 2. Ru催化的酰胺基芳烃碳氢，碳氮和碳氧键功能化：C-B形成，碳-碳铃木交叉偶联和加氢脱甲氧基化
6. Facile synthesis of 1-alkoxy-1H-benzo- and 7-azabenzotriazoles from peptide coupling agents mechanistic studies and synthetic applications [O] . Mahesh K Lakshman, Manish K Singh, Mukesh Kumar, 2014

机译：从肽偶联剂轻松合成1-烷氧基-1H-苯并-和7-氮杂苯并三唑机理研究和合成应用
7. Rapid and efficient synthesis of the penta-peptide of elastin protein and peptides containing highly hindered α,α-dialkyl amino acids employing Fmoc-amino acid chlorides under microwave irradiation in solution phase [O] . Subramanyam J. Tantry, R. V. Ramana Rao, V. V. Suresh Babu 2005

机译：使用Fmoc-氨基酸氯化物在溶液相微波辐射下快速有效地合成弹性蛋白的五肽和含有高度受阻α，α-二烷基氨基酸的肽

HOAt.DCHA as co-coupling agent in the synthesis of peptides employing Fmoc-amino acid chlorides as coupling agents: Application to the synthesis of β-casomorphin

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