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] Synthetic sulfoglycolipids targeting the serine-threonine protein kinase Akt
    Costa, Barbara
    Dangate, Milind
    Vetro, Maria
    Donvito, Giulia
    Gabrielli, Luca
    Amigoni, Loredana
    Cassinelli, Giuliana
    Lanzi, Cinzia
    Ceriani, Michela
    De Gioia, Luca
    Filippi, Giulia
    Cipolla, Laura
    Zaffaroni, Nadia
    Perego, Paola
    Colombo, Diego
    BIOORGANIC & MEDICINAL CHEMISTRY, 2016, 24 (16) : 3396 - 3405
  • [32] Development and Applications of Ligation-Desulfurization-Desulfurization Strategy in Protein Chemical Synthesis
    Xu, Ling
    Yin, Panpan
    Lu, Xianfu
    Li, Yiming
    CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2024, 45 (08):
  • [33] Cysteine/Penicillamine Ligation Independent of Terminal Steric Demands for Chemical Protein Synthesis
    Tan, Yi
    Li, Jiasheng
    Jin, Kang
    Liu, Jiamei
    Chen, Ziyong
    Yang, Jun
    Li, Xuechen
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (31) : 12741 - 12745
  • [34] Azole reagents enabled ligation of peptide acyl pyrazoles for chemical protein synthesis
    Liao, Peisi
    He, Chunmao
    CHEMICAL SCIENCE, 2024, 15 (21) : 7965 - 7974
  • [35] Chemical Protein Synthesis by Kinetically Controlled Ligation of Peptide O-Esters
    Zheng, Ji-Shen
    Cui, Hong-Kui
    Fang, Ge-Min
    Xi, Wei-Xian
    Liu, Lei
    CHEMBIOCHEM, 2010, 11 (04) : 511 - 515
  • [36] Glycocluster Synthesis by Native Chemical Ligation
    Wehner, Johannes W.
    Lindhorst, Thisbe K.
    SYNTHESIS-STUTTGART, 2010, (18): : 3070 - 3082
  • [37] Synthesis of native proteins by chemical ligation
    Dawson, PE
    Kent, SBH
    ANNUAL REVIEW OF BIOCHEMISTRY, 2000, 69 : 923 - 960
  • [38] Modern tools for the chemical ligation and synthesis of modified peptides and proteins
    Gentilucci, Luca
    Tosi, Pierluigi
    Bauer, Adriano
    De Marco, Rossella
    FUTURE MEDICINAL CHEMISTRY, 2016, 8 (18) : 2287 - 2304
  • [39] Synthesis of Thiazolidine Thioester Peptides and Acceleration of Native Chemical Ligation
    Dheur, Julien
    Ollivier, Nathalie
    Melnyk, Oleg
    ORGANIC LETTERS, 2011, 13 (06) : 1560 - 1563
  • [40] α-Selective Lysine Ligation and Application in Chemical Synthesis of Interferon Gamma
    Dao, Yuankun
    Han, Lin
    Wang, Hamann
    Dong, Suwei
    ORGANIC LETTERS, 2019, 21 (09) : 3265 - 3270