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Synthesis of 2H, 13C, 15N-isotomers of branched-chain amino acids(1)

✍ Scribed by Sun-Shine Yuan Kor

Publisher: John Wiley and Sons
Year: 1983
Tongue: French
Weight: 254 KB
Volume: 20
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.2580200205

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✦ Synopsis

Abstract

Synthetic schemes for 2(S,R)‐amino‐3‐D~3~methylpentanoic acid, 2(S,R)‐amino‐3‐^13^Cmethyl‐[4‐^13^C]pentanoic acid (isoleucine) and 1‐^13^C,^15^N‐leucine are described. The side chain labeled isoleucines were constructed by first alkylating 2,4,4‐trimethyl‐2‐oxazoline with appropriate labeled alkyl halides and then reducing the resultant oxazolines to the aldehydes. Strecker synthesis yielded a mixture of isoleucine and alloisoleucine which was separated via the N‐acetyl derivatives. In a separate sequence, Strecker synthesis using 3‐methylbutanal, [^13^C]cyanide and [^15^N]ammonium hydroxide, followed by acid hydrolysis, gave [1‐^13^C, ^15^N]leucine amide. This amide was resolved by leucine aminopeptidase to produce 1‐^13^C,^15^N‐leucine. Similar schemes were used for the synthesis of [1‐^13^C] or ^15^N‐leucine and [1‐^13^C] or ^15^N‐valine.

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