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Synthetic Circularized Analogues of Bovine Pancreatic Trypsin Inhibitor
Author(s) -
TullaPuche Judit,
Getun Irina V.,
Alsina Jordi,
Albericio Fernando,
Barany George
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400507
Subject(s) - chemistry , native chemical ligation , trypsin , residue (chemistry) , trypsin inhibitor , stereochemistry , side chain , ligation , combinatorial chemistry , biochemistry , chemical synthesis , organic chemistry , enzyme , in vitro , microbiology and biotechnology , biology , polymer
Two cyclic analogues of the protein bovine pancreatic trypsin inhibitor (BPTI), c‐[R] Smc and c‐Cys5[R] Abu , have been synthesized. For the first target, a semisynthetic approach featured a cyclization that took advantage of the constraint imposed by the three disulfides of the native protein. For the second target, an entirely unstructured 58‐residue thiolester, prepared by total synthesis with mild Fmoc chemistry and a side‐chain anchoring strategy, was cyclized by native chemical ligation. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)