Racemization studies of Fmoc-Cys-(Trt)-OH during stepwise Fmoc-solid phase peptide synthesis

被引：45
|
作者：
Kaiser, T
Nicholson, GJ
Kohlbau, HJ
Voelter, W
机构：
[1] UNIV TUBINGEN,INST PHYSIOL CHEM,PHYS BIOCHEM ABT,D-72076 TUBINGEN,GERMANY
[2] UNIV TUBINGEN,INST ORGAN CHEM,D-72076 TUBINGEN,GERMANY
来源：
TETRAHEDRON LETTERS | 1996年 / 37卷 / 08期
关键词：
D O I：
10.1016/0040-4039(95)02406-9
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
In conventional stepwise Fmoc solid phase peptide synthesis, diisopropylethylamine (DIEA) base-catalyzed acylation methods lead to considerable amounts of racemization of Fmoc-Cys(Trt) residues during the activation/coupling process. The epimerization can be reduced to a negligible degree, via. a base-free activation step.
引用
收藏
页码：1187 / 1190
页数：4
相关论文
共 50 条
  • [41] Improved Fmoc Solid-Phase Peptide Synthesis of Oxytocin with High Bioactivity
    Sun, Pengcheng
    Tang, Wenli
    Huang, Yu
    Hu, Bi-Huang
    SYNLETT, 2017, 28 (14) : 1780 - 1784
  • [42] Studies of esterification of Wang resin and fmoc/t-Bu tyrosin in solid phase peptide synthesis
    College of Life Science and Pharmacy, Nanjing University of Technology, Nanjing 210009, China
    Lizi Jiaohuan Yu Xifu, 2006, 3 (216-223):
  • [43] Racemization in stepwise solid-phase peptide synthesis at elevated temperatures
    Souza, MP
    Tavares, MFM
    Miranda, MTM
    TETRAHEDRON, 2004, 60 (21) : 4671 - 4681
  • [44] Deprotection Strategies for Thioimidates during Fmoc Solid-Phase Peptide Synthesis: A Safe Route to Thioamides
    Camacho, Luis A., III
    Nguyen, Yen H.
    Turner, John
    VanVeller, Brett
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (23): : 15309 - 15314
  • [45] Peptide thioester preparation by Fmoc solid phase peptide synthesis for use in native chemical ligation
    Clippingdale, AB
    Barrow, CJ
    Wade, JD
    JOURNAL OF PEPTIDE SCIENCE, 2000, 6 (05) : 225 - 234
  • [46] PREPARATION AND USE OF N-FMOC-O-TRT-HYDROXYAMINO ACIDS FOR SOLID-PHASE SYNTHESIS OF PEPTIDES
    BARLOS, K
    GATOS, D
    KOUTSOGIANNI, S
    SCHAFER, W
    STAVROPOULOS, G
    YAO, WQ
    TETRAHEDRON LETTERS, 1991, 32 (04) : 471 - 474
  • [47] DESIGN AND SYNTHESIS OF A CIS-GLY-PRO, TYPE-VI TURN, DIPEPTIDE MIMETIC AND ITS USE IN FMOC-SOLID PHASE PEPTIDE-SYNTHESIS
    GRAMBERG, D
    ROBINSON, JA
    TETRAHEDRON LETTERS, 1994, 35 (06) : 861 - 864
  • [48] Synthesis of Fmoc-protected dicarboxyglutamic acid and its use in solid phase peptide synthesis
    Nelson, JW
    Capriotti, LA
    Schneider, JP
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U832 - U832
  • [49] Replacing piperidine in solid phase peptide synthesis: effective Fmoc removal by alternative bases
    Martelli, Giulia
    Cantelmi, Paolo
    Palladino, Chiara
    Mattellone, Alexia
    Corbisiero, Dario
    Fantoni, Tommaso
    Tolomelli, Alessandra
    Macis, Marco
    Ricci, Antonio
    Cabri, Walter
    Ferrazzano, Lucia
    GREEN CHEMISTRY, 2021, 23 (20) : 8096 - 8107
  • [50] An improved deblocking agent for direct Fmoc solid-phase synthesis of peptide thioesters
    Bu, XZ
    Xie, GY
    Law, CW
    Guo, ZH
    TETRAHEDRON LETTERS, 2002, 43 (13) : 2419 - 2422
12345