Synthesis of S‐benzyl‐DL‐[1‐13C]cysteine and its incorporation into oxytocin and [8‐arginlne]vasopressin and related compounds by total synthesis. Separation of diastekeoisomers by partition chromatography and HPLC

Victor J. Hruby, V. Viswanatha, Young C.S. Yang

Research output: Contribution to journalArticle

5 Scopus citations

Abstract

S‐Benzyl‐DL‐[1‐13C]cysteine was prepared from Na13CN 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‐[1‐13C]cystine]oxytocin, [1‐hemi‐D‐[1‐13C]‐cystine]oxytocin, [1‐hemi‐[1‐13C]cystine, 8‐arginine]vasopressin, [1‐hemi‐D[1‐13C]cystine, 8‐arginine]vasopressin, [6‐hemi‐[1‐13C]cystine]oxytocin, [6‐hemi‐D‐[1‐13C]cystine]oxytocin, [1‐hemi‐D‐[1‐13C]cystine, 3‐D‐leucine]‐oxytocin, and [1‐hemi‐[1‐13C]cystine, 3‐D‐leucine]oxytocin.

Original languageEnglish (US)
Pages (from-to)801-812
Number of pages12
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume17
Issue number6
DOIs
StatePublished - Jan 1 1980

Keywords

  • Carbon‐13
  • labeled peptide hormones
  • oxytocin
  • solid phase synthesis

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Radiology Nuclear Medicine and imaging
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

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