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Strategy for the synthesis of large peptides: An application to the total synthesis of human parathyroid hormone [hPTH(1–84)]
Author(s) -
Kimura T.,
Takai M.,
Masui Y.,
Morikawa T.,
Sakakibara S.
Publication year - 1981
Publication title -
biopolymers
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.556
H-Index - 125
eISSN - 1097-0282
pISSN - 0006-3525
DOI - 10.1002/bip.1981.360200907
Subject(s) - carbodiimide , chemistry , parathyroid hormone , side chain , condensation , peptide synthesis , combinatorial chemistry , peptide , chromatography , hormone , organic chemistry , biochemistry , calcium , physics , thermodynamics , polymer
A strategy suitable for the synthesis of larger peptides is proposed. It involves the following four considerations: (1) all of the side‐chain functional groups are protected by benzyl‐type protective groups; (2) a water‐soluble carbodiimide, 1‐ethyl‐3‐(3‐dimethylaminopropyl)‐carbodiimide, is used for the fragment‐condensation reactions together with 1‐hydroxybenzotriazole as the additive; (3) all the protective groups are cleaved simultaneously by the HF method in the final stage of the synthesis; and (4) side products formed are detected and removed by an efficient high‐performance liquid chromatography procedure. The usefulness of these procedures is demonstrated taking the synthesis of human parathyroid hormone [hPTH(1–84)] as an example.