A convenient synthesis of 2S, 3S‐[3‐2H]‐serine and 2S, 3R‐[2, 3‐2H2]‐serine

Lawrence Slieker, Stephen Benkovic

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Abstract

Both 2S, 3R‐[2, 3‐2H2]‐serine 5 and 2S, 3S‐[3‐2H]‐serine 6 have been prepared from (E)‐methyl‐[2, 3.‐2H2]‐acrylate and (Z)‐ethyl‐[3‐2H]‐acrylate, respectively. The acrylate esters were converted to a mixture of isomeric bromohydrins by treatment with N‐bromoacetamide. The ratio of 2‐bromo‐3‐hydroxy species to the 2‐hydroxy‐3‐bromo isomer was approximately 3:1. Conversion to the corresponding azido alcohols by treatment with NaN3 followed by catalytic reduction over Pd gave the alkyl esters of serine and isoserine. Purification and hydrolysis yielded serine in typically 20–25% yield from methyl or ethyl acrylate. Resolution was accomplished enzymatically by hog kidney acylase I treatment of the N‐acetyl derivative. Absolute configuration was determined by 1H NMR and the ratio of proton intensity in the diastereotopic positions at C–3 were measured to be HS/HR = 11 for 5 and HR/HS = 4.4 for 6.

Original languageEnglish (US)
Pages (from-to)647-657
Number of pages11
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume19
Issue number5
DOIs
StatePublished - Jan 1 1982

All Science Journal Classification (ASJC) codes

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

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