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CLipPA 化学法合成脂肽

Synthesis of Lipopeptides by CLipPA Chemistry.

机构信息

School of Chemical Sciences, The University of Auckland, Auckland, New Zealand.

School of Biological Sciences, The University of Auckland, Auckland, New Zealand.

出版信息

Methods Mol Biol. 2021;2355:253-263. doi: 10.1007/978-1-0716-1617-8_19.

DOI:10.1007/978-1-0716-1617-8_19
PMID:34386963
Abstract

Lipidation of polypeptides with a fatty acid to form N-linked lipopeptides can be a time consuming process due to the need to mask other reactive function groups present on the side chains of amino acids. Cysteine Lipidation on a Peptide or Amino acid (CLipPA) technology enables the direct lipidation of unprotected peptides containing a free thiol group to afford S-lipidated lipopeptides. A generalized procedure for the synthesis of S-lipopeptides is described which facilities rapid preparation of tens of analogs of lipopeptides from a single thiolated polypeptide precursor.

摘要

将脂肪酸酰化多肽形成 N-连接的脂肽是一个耗时的过程,因为需要掩蔽氨基酸侧链上存在的其他反应性功能基团。肽或氨基酸的半胱氨酸脂化 (CLipPA) 技术可使含有游离巯基的未保护肽直接脂化,得到 S-脂肽。本文描述了一种 S-脂肽合成的通用方法,可从单个巯基化多肽前体快速制备数十种脂肽类似物。

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Synthesis of Lipopeptides by CLipPA Chemistry.CLipPA 化学法合成脂肽
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本文引用的文献

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"CLipP"ing on lipids to generate antibacterial lipopeptides.“剪辑”脂质以生成抗菌脂肽。
Chem Sci. 2020 May 20;11(22):5759-5765. doi: 10.1039/d0sc01814g.
2
Thiol-ene Enabled Chemical Synthesis of Truncated -Lipidated Teixobactin Analogs.硫醇-烯介导的截短型脂化替考拉宁类似物的化学合成。
Front Chem. 2020 Aug 4;8:568. doi: 10.3389/fchem.2020.00568. eCollection 2020.
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Variable-Length Ester-Based Staples for α-Helical Peptides by Using A Double Thiol-ene Reaction.基于可变长度酯基的α-螺旋多肽订书钉的双硫醇-烯反应法。
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4
Direct synthesis of cyclic lipopeptides using intramolecular native chemical ligation and thiol-ene CLipPA chemistry.使用分子内天然化学连接和硫醇-烯 CLipPA 化学直接合成环状脂肽。
Org Biomol Chem. 2020 Apr 15;18(15):2838-2844. doi: 10.1039/d0ob00203h.
5
Chemical Strategies for Half-Life Extension of Biopharmaceuticals: Lipidation and Its Alternatives.生物制药半衰期延长的化学策略:脂质化及其替代方法。
ACS Med Chem Lett. 2018 Jun 15;9(7):577-580. doi: 10.1021/acsmedchemlett.8b00226. eCollection 2018 Jul 12.
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Daptomycin antibiotic production processes in fed-batch fermentation by Streptomyces roseosporus NRRL11379 with precursor effect and medium optimization.利用前体效应和培养基优化,在玫瑰孢链霉菌NRRL11379的补料分批发酵中生产达托霉素抗生素的工艺
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Sequence-independent control of peptide conformation in liposomal vaccines for targeting protein misfolding diseases.脂质体疫苗中肽构象的序列无关控制,用于靶向蛋白质错误折叠疾病。
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Exploiting enzymatic regioselectivity: a facile methodology for the synthesis of polyhydroxylated hybrid compounds.利用酶的区域选择性:一种合成多羟基化杂合化合物的简便方法。
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