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Synthesis of S‐benzyl‐DL‐[1‐ 13 C]cysteine and its incorporation into oxytocin and [8‐arginlne]vasopressin and related compounds by total synthesis. Separation of diastekeoisomers by partition chromatography and HPLC
Author(s) -
Hruby Victor J.,
Viswanatha V.,
Yang Young C. S.
Publication year - 1980
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580170607
Subject(s) - chemistry , oxytocin , cystine , vasopressin , cysteine , arginine , high performance liquid chromatography , leucine , peptide synthesis , stereochemistry , peptide , chromatography , amino acid , biochemistry , medicine , enzyme
S‐Benzyl‐DL‐[1‐ 13 C]cysteine was prepared from Na 13 CN by a three step synthesis and converted to the t‐butyloxycarbonyl derivative which was suitable for use in peptide synthesis. This compound was incorporated into the 1 and 6 positions of a variety of oxytocin and [8‐arginine]vasopressin derivatives and analogues via total synthesis using the solid phase method. The compounds were separated and purified by partition chromatography on Sephadex and their purity was checked by high pressure liquid chromatography. The compounds synthesized include [1‐hemi‐[1‐ 13 C]cystine]oxytocin, [1‐hemi‐ D ‐[1‐ 13 C]‐cystine]oxytocin, [1‐hemi‐[1‐ 13 C]cystine, 8‐arginine]vasopressin, [1‐hemi‐ D [1‐ 13 C]cystine, 8‐arginine]vasopressin, [6‐hemi‐[1‐ 13 C]cystine]oxytocin, [6‐hemi‐ D ‐[1‐ 13 C]cystine]oxytocin, [1‐hemi‐ D ‐[1‐ 13 C]cystine, 3‐ D ‐leucine]‐oxytocin, and [1‐hemi‐[1‐ 13 C]cystine, 3‐ D ‐leucine]oxytocin.