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Solid‐phase Synthesis of C‐Terminal Peptide Amino Alcohols
Author(s) -
Neugebauer Witold,
Escher Emanuel
Publication year - 1989
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19890720620
Subject(s) - chemistry , cleave , hydrolysis , solid phase synthesis , terminal (telecommunication) , peptide , succinic acid , amino acid , cleavage (geology) , alcohol , peptide synthesis , phase (matter) , enkephalin , stereochemistry , combinatorial chemistry , organic chemistry , biochemistry , enzyme , opioid , telecommunications , receptor , geotechnical engineering , fracture (geology) , computer science , engineering
The solid‐phase syntheses of enkephalin and somatostatin analogues with C‐terminal OH functions instead of the normal carboxylates are described. The OH function of the N‐terminal amino alcohol was acylated with succinic acid and esterified to the solid support. Normal Boc‐TFA solid‐phase strategy can be applied to build up and cleave these peptides. The succinic ‘handle’ can be removed by mild basic hydrolysis after cleavage.