Premium
Synthesis of (3RS)‐[2,3‐ 3 H 2 (N)]‐β‐leucine
Author(s) -
Aberhart D. John,
Lin HorngJau
Publication year - 1983
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.2580200507
Subject(s) - chemistry , leucine , hydrolysis , tritium , substrate (aquarium) , product distribution , stereochemistry , amino acid , chromatography , organic chemistry , catalysis , biochemistry , physics , oceanography , nuclear physics , geology
(3RS)‐[2,3‐ 3 H 2 (N)]‐β‐Leucine, a substrate for assay of leucine 2,3‐amino‐mutase, has been synthesized. Ethyl (Z)‐3‐acetamido‐4‐methylpent‐2‐enoate was reduced with 3 H 2 gas over Pd(C) to (3RS)‐[2,3‐ 3 H 2 (N)]‐β‐leucine ethyl ester, which was hydrolyzed with HCl‐H 2 O to (3RS)‐[2,3‐ 3 H 2 (N)]‐β‐leucine. The crude product was purified, on a small scale by preparative HPLC. Analysis of the crude product by 3 H NMR, and of the purified product by equilibration analysis indicated a tritium distribution of ca 70% at C‐3 and 30% at C‐2.