Synthesis of [4a‐13C]‐6‐methyltetrahydropterin

Robert A. Lazarus; Michael A. Sulewski; Stephen J. Benkovic

doi:10.1002/jlcr.2580191009

Synthesis of [4a‐¹³C]‐6‐methyltetrahydropterin

Robert A. Lazarus, Michael A. Sulewski, Stephen J. Benkovic

Chemistry

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8 Scopus citations

Abstract

The synthesis of [4a‐¹³C]‐6‐methyltetrahydropterin, a synthetic cofactor for phenylalanine hydroxylase, is described. [2‐¹³C]‐ethyl bromoacetate was converted in four steps to [5‐¹³C]‐2,4‐diamino‐6‐hydroxypyrimidine in 86% yield. The latter was nitrosated, reduced, condensed with pyruvic aldehyde, and reduced to afford pure [4a‐¹³C]‐6‐methyltetrahydropterin in a net overall yield of 16%.

Original language	English (US)
Pages (from-to)	1189-1195
Number of pages	7
Journal	Journal of Labelled Compounds and Radiopharmaceuticals
Volume	19
Issue number	10
DOIs	https://doi.org/10.1002/jlcr.2580191009
State	Published - Oct 1982

All Science Journal Classification (ASJC) codes

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

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title = "Synthesis of [4a‐13C]‐6‐methyltetrahydropterin",

abstract = "The synthesis of [4a‐13C]‐6‐methyltetrahydropterin, a synthetic cofactor for phenylalanine hydroxylase, is described. [2‐13C]‐ethyl bromoacetate was converted in four steps to [5‐13C]‐2,4‐diamino‐6‐hydroxypyrimidine in 86% yield. The latter was nitrosated, reduced, condensed with pyruvic aldehyde, and reduced to afford pure [4a‐13C]‐6‐methyltetrahydropterin in a net overall yield of 16%.",

author = "Lazarus, {Robert A.} and Sulewski, {Michael A.} and Benkovic, {Stephen J.}",

year = "1982",

month = oct,

doi = "10.1002/jlcr.2580191009",

language = "English (US)",

volume = "19",

pages = "1189--1195",

journal = "Journal of Labelled Compounds and Radiopharmaceuticals",

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T1 - Synthesis of [4a‐13C]‐6‐methyltetrahydropterin

AU - Lazarus, Robert A.

AU - Sulewski, Michael A.

AU - Benkovic, Stephen J.

PY - 1982/10

Y1 - 1982/10

N2 - The synthesis of [4a‐13C]‐6‐methyltetrahydropterin, a synthetic cofactor for phenylalanine hydroxylase, is described. [2‐13C]‐ethyl bromoacetate was converted in four steps to [5‐13C]‐2,4‐diamino‐6‐hydroxypyrimidine in 86% yield. The latter was nitrosated, reduced, condensed with pyruvic aldehyde, and reduced to afford pure [4a‐13C]‐6‐methyltetrahydropterin in a net overall yield of 16%.

AB - The synthesis of [4a‐13C]‐6‐methyltetrahydropterin, a synthetic cofactor for phenylalanine hydroxylase, is described. [2‐13C]‐ethyl bromoacetate was converted in four steps to [5‐13C]‐2,4‐diamino‐6‐hydroxypyrimidine in 86% yield. The latter was nitrosated, reduced, condensed with pyruvic aldehyde, and reduced to afford pure [4a‐13C]‐6‐methyltetrahydropterin in a net overall yield of 16%.

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DO - 10.1002/jlcr.2580191009

M3 - Article

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VL - 19

SP - 1189

EP - 1195

JO - Journal of Labelled Compounds and Radiopharmaceuticals

JF - Journal of Labelled Compounds and Radiopharmaceuticals

IS - 10

ER -

Synthesis of [4a‐¹³C]‐6‐methyltetrahydropterin

Abstract

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