Facilitating Subtiligase-Catalyzed Peptide Ligation Reactions by Using Peptide Thioester Substrates

被引：15
|
作者：
Tan, Xiaohong [1 ,2 ]
Yang, Renliang [3 ]
Liu, Chuan-Fa [3 ]
机构：
[1] Carnegie Mellon Univ, Dept Chem, 4400 5th Ave, Pittsburgh, PA 15213 USA
[2] Carnegie Mellon Univ, Ctr Nucle Acids Sci & Technol, Pittsburgh, PA 15213 USA
[3] Nanyang Technol Univ, Sch Biol Sci, Div Chem Biol & Biotechnol, Singapore 637551, Singapore
来源：
ORGANIC LETTERS | 2018年 / 20卷 / 21期
关键词：
NATIVE CHEMICAL LIGATION; SOLID-PHASE SYNTHESIS; UNPROTECTED PEPTIDES; PROTEIN-SYNTHESIS; THIOACIDS; LIGASE; SCOPE;
D O I：
10.1021/acs.orglett.8b02747
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
By facilitating formation of the aryl-enzyme intermediate, peptide thioesters can largely promote subtiligase-catalyzed ligation reactions over their ester counterparts. This offers a significant addition to the repertoire of enzymatic methods for protein chemical synthesis and modification.
引用
收藏
页码：6691 / 6694
页数：4
相关论文
共 50 条
  • [31] Peptide αthioester formation using standard Fmoc-chemistry
    von Eggelkraut-Gottanka, R
    Klose, A
    Beck-Sickinger, AG
    Beyermann, M
    BIOPOLYMERS, 2003, 71 (03) : 352 - 353
  • [32] Peptide αthioester formation using standard Fmoc-chemistry
    von Eggelkraut-Gottanka, R
    Klose, A
    Beck-Sickinger, AG
    Beyermann, M
    TETRAHEDRON LETTERS, 2003, 44 (17) : 3551 - 3554
  • [33] Biocatalyst-catalyzed peptide synthesis using inverse substrates AS acyl donor
    Sekizaki, Haruo
    Fuchise, Tomoyoshi
    Kojoma, Mareshige
    Toyota, Eiko
    JOURNAL OF PEPTIDE SCIENCE, 2008, 14 (08) : 168 - 168
  • [34] Bioorthogonal Peptide Macrocyclization Using Oxime Ligation
    Davies, Lani J.
    Shuttleworth, Laura M.
    Zhang, Xiaobai
    Peng, Sherry
    Nitsche, Christoph
    ORGANIC LETTERS, 2023, 25 (16) : 2806 - 2809
  • [35] Incorporation of selenocysteine into proteins using peptide ligation
    Hondal, RJ
    PROTEIN AND PEPTIDE LETTERS, 2005, 12 (08): : 757 - 764
  • [36] Use of Model Peptide Reactions for the Characterization of Kinetically Controlled Ligation
    Lee, Joongoo
    Kwon, Yoonjin
    Pentelute, Brad L.
    Bang, Duhee
    BIOCONJUGATE CHEMISTRY, 2011, 22 (08) : 1645 - 1649
  • [37] EFFICIENT PEPTIDE LIGATION USING AZIDO- AND PYRUVOYL-PROTECTED PEPTIDES VIA THE Ag plus -FREE THIOESTER METHOD
    Katayama, H.
    Hojo, H.
    Ohira, T.
    Nakahara, Y.
    Nakahara, Y.
    BIOPOLYMERS, 2009, 92 (04) : 372 - 372
  • [38] An efficient Fmoc-SPPS approach for the generation of thioester peptide precursors for use in native chemical ligation
    Blanco-Canosa, Juan B.
    Dawson, Philip E.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (36) : 6851 - 6855
  • [39] ACYL TRANSPEPTIDATION AND HYDROLYTIC REACTIONS CATALYZED BY ENDOTHIA-PARASITICA PROTEASE WITH SMALL PEPTIDE-SUBSTRATES
    LEE, SL
    WHITAKER, JR
    JOURNAL OF FOOD BIOCHEMISTRY, 1979, 3 (01) : 53 - 72
  • [40] ACCUMULATION OF ACYL-ENZYME IN DD-PEPTIDASE-CATALYZED REACTIONS WITH ANALOGS OF PEPTIDE-SUBSTRATES
    JAMIN, M
    ADAM, M
    DAMBLON, C
    CHRISTIAENS, L
    FRERE, JM
    BIOCHEMICAL JOURNAL, 1991, 280 : 499 - 506
12345