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Synthesis of [2‐ p ‐Fluorophenylalanine]oxytocin and its Desamino Analogue Using the S‐Acetamidomethyl Protecting Group
Author(s) -
Marbach Peter,
Rudinger Josef
Publication year - 1974
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.19740570215
Subject(s) - chemistry , uterotonic , oxytocin , protecting group , cysteine , stereochemistry , disulfide bond , combinatorial chemistry , organic chemistry , biochemistry , medicine , alkyl , enzyme
[2‐ p ‐Fluorophenylalanine]oxytocin ( 1a ), desamino‐[2‐ p ‐fluorophenylalanine]oxytocin ( 1b ), and desamino‐oxytocin ( 2 ) have been synthesised via intermediates containing S‐acetamidomethyl‐cysteine. The protected linear peptides were built up using both stepwise and fragment‐condensation procedures, and the S‐protecting groups were removed by iodine with simultaneous formation of the disulfide bridge. The uterotonic activities in vitro of the analogues have been determined. The close similarity of the 19 F‐NMR. spectra indicates that the p ‐fluorbenzyl side chain is freely exposed to the solvent in the disulfide‐bridged hormone analogues as well as in their S‐protected, acyclic precursors.