Protein chemical synthesis by serine and threonine ligation

被引:221
|
作者
Zhang, Yinfeng [1 ]
Xu, Ci [1 ]
Lam, Hiu Yung [1 ]
Lee, Chi Lung [1 ]
Li, Xuechen [1 ]
机构
[1] Univ Hong Kong, Dept Chem, Hong Kong, Hong Kong, Peoples R China
关键词
synthetic protein; acyl transfer; chemoselective ligation; PRIOR THIOL CAPTURE; INTRAMOLECULAR O; N-ACYL TRANSFER; PEPTIDE-BOND FORMATION; STAUDINGER LIGATION; SIDE-CHAIN; CYSTEINE; ACYLPHOSPHATASE; STRATEGIES; THIOESTER; MECHANISM;
D O I
10.1073/pnas.1221012110
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
An efficient method has been developed for the salicylaldehyde ester-mediated ligation of unprotected peptides at serine (Ser) or threonine (Thr) residues. The utility of this peptide ligation approach has been demonstrated through the convergent syntheses of two therapeutic peptides-ovine-corticoliberin and Forteo-and the human erythrocyte acylphosphatase protein (similar to 11 kDa). The requisite peptide salicylaldehyde ester precursor is prepared in an epimerization-free manner via Fmoc-solid-phase peptide synthesis.
引用
收藏
页码:6657 / 6662
页数:6
相关论文
共 50 条
  • [31] Chemical Protein Synthesis by Native Chemical Ligation and Variations Thereof
    Wang, Siyao
    Thopate, Yogesh Abaso
    Zhou, Qingqing
    Wang, Ping
    CHINESE JOURNAL OF CHEMISTRY, 2019, 37 (11) : 1181 - 1193
  • [32] Realizing serine/threonine ligation: scope and limitations and mechanistic implication thereof
    Wong, Clarence T. T.
    Li, Tianlu
    Lam, Hiu Yung
    Zhang, Yinfeng
    Li, Xuechen
    FRONTIERS IN CHEMISTRY, 2014, 2
  • [33] Modern Extensions of Native Chemical Ligation for Chemical Protein Synthesis
    Malins, Lara R.
    Payne, Richard J.
    PROTEIN LIGATION AND TOTAL SYNTHESIS I, 2015, 362 : 27 - 87
  • [34] Total synthesis of the serine/threonine-specific protein phosphatase inhibitor tautomycin
    Sheppeck, JE
    Liu, W
    Chamberlin, AR
    JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (02): : 387 - 398
  • [35] Total Synthesis of the Serine/Threonine-Specific Protein Phosphatase Inhibitor Tautomycin
    Sheppeck, J. E.
    Liu, W.
    Chamberlin, A. R.
    Journal of Organic Chemistry, 62 (02):
  • [36] Native chemical ligation in protein synthesis and semi-synthesis
    Conibear, Anne C.
    Watson, Emma E.
    Payne, Richard J.
    Becker, Christian F. W.
    CHEMICAL SOCIETY REVIEWS, 2018, 47 (24) : 9046 - 9068
  • [37] MECHANISMS OF REGULATION OF SERINE THREONINE PROTEIN PHOSPHATASES
    DEPAOLIROACH, AA
    FASEB JOURNAL, 1994, 8 (07): : A1239 - A1239
  • [38] CHARACTERIZATION OF SERINE THREONINE PROTEIN PHOSPHATASE INHIBITORS
    HONKANEN, RE
    CODISPOTI, BA
    TSE, K
    BOYNTON, AL
    JOURNAL OF CELLULAR BIOCHEMISTRY, 1993, : 310 - 310
  • [39] Mycobacterium tuberculosis Serine/Threonine Protein Kinases
    Prisic, Sladjana
    Husson, Robert N.
    MICROBIOLOGY SPECTRUM, 2014, 2 (05):
  • [40] Serine threonine protein phosphatases and the β cells of the pancreas
    Parameswara, VK
    Easom, RA
    FASEB JOURNAL, 2002, 16 (05): : A914 - A914