Synthesis of Cysteine-Containing Polypeptide Using a Peptide Thioester Containing a Cys(Acm) Residue

Synthesis of Cysteine-Containing Polypeptide Using a Peptide Thioester Containing a Cys(Acm) Residue
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使用含有Cys(Acm)残基的肽硫酯合成含有半胱氨酸的多肽

DOI:
10.1246/bcsj.69.3331
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发表时间:
1996
影响因子:
4
通讯作者:
S. Aimoto
S. Aimoto
中科院分区:
化学3区
文献类型:
--
作者:
T. Kawakami;Shuji Kogure;S. Aimoto

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开发了一种使用通过Boc固相法获得的含Cys(Acm)的肽硫酯制备含半胱氨酸的多肽的方法。为了证明所开发的方法的实用性,合成了由52个氨基酸残基组成的人肾上腺髓质素。用固相法合成了Boc-[Cys(Acm)16]-肾上腺髓质素(1-19)-SCH 2CH 2CO-β-Ala-NH 2和[Cys(Acm)21,Lys(Boc)25,36,38,46]-肾上腺髓质素(20-52)。这些肽段在银离子、添加剂和碱的存在下缩合。当HOBt或HOOBt用作添加剂时,片段偶联进行,Acm基团的分解可忽略不计,得到所需产物。还描述了在碱性条件下在银离子和水存在下从半胱氨酸残基中除去S-Acm基团的方法。
A method was developed for the preparation of a cysteine-containing polypeptide, using a Cys(Acm)-containing peptide thioester obtained by a Boc solid-phase method. To demonstrate the utility of the developed method, human adrenomedullin consisting of 52 amino acid residues was synthesized. A peptide thioester, Boc–[Cys(Acm)16]–adrenomedullin(1—19)-SCH2CH2CO-β-Ala–NH2, and [Cys(Acm)21, Lys(Boc)25,36,38,46]-adrenomedullin(20—52) were prepared by conventional solid-phase methods. These peptide segments were condensed in the presence of silver ions, an additive, and a base. When HOBt or HOOBt was used as an additive, the segment coupling proceeded with negligible decomposition of Acm groups to give the desired product. A method for the removal of S-Acm groups from cysteine residues under basic conditions in the presence of silver ions and water, is also described.
DOI: 10.1039/c39890000283
发表时间: 1989
期刊: Journal of The Chemical Society, Chemical Communications
影响因子: --
作者:
N. Fujii;A. Otaka;Toshihiro Watanabe;A. Okamachi;H. Tamamura;H. Yajima;Y. Inagaki;M. Nomizu;K. Asano
通讯作者: N. Fujii;A. Otaka;Toshihiro Watanabe;A. Okamachi;H. Tamamura;H. Yajima;Y. Inagaki;M. Nomizu;K. Asano
DOI: 10.1006/bbrc.1993.1451
发表时间: 1993-04-30
影响因子: 3.1
作者:
KITAMURA, K;KANGAWA, K;ETO, T
通讯作者: ETO, T
H.Hojo:“含 S-保护的半胱氨酸肽硫酯的制备及其在酿酒酵母 DNA 指导的 RNA 聚合酶 II 中合成 Barnase 样结构域的用途”Bull.Chem.Soc.Jpn.68。
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