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Synthesis of [4a‐ 13 C]‐6‐methyltetrahydropterin
Author(s) -
Lazarus Robert A.,
Sulewski Michael A.,
Benkovic Stephen J.
Publication year - 1982
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.2580191009
Subject(s) - chemistry , yield (engineering) , aldehyde , stereochemistry , ethyl bromoacetate , cofactor , organic chemistry , enzyme , catalysis , materials science , metallurgy
The synthesis of [4a‐ 13 C]‐6‐methyltetrahydropterin, a synthetic cofactor for phenylalanine hydroxylase, is described. [2‐ 13 C]‐ethyl bromoacetate was converted in four steps to [5‐ 13 C]‐2,4‐diamino‐6‐hydroxypyrimidine in 86% yield. The latter was nitrosated, reduced, condensed with pyruvic aldehyde, and reduced to afford pure [4a‐ 13 C]‐6‐methyltetrahydropterin in a net overall yield of 16%.