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Efficient syntheses of 13C- and 14C-labelled 5-benzyl and 5-indolylmethyl L-hydantoins

✍ Scribed by Simon G. Patching

Publisher
John Wiley and Sons
Year
2010
Tongue
French
Weight
164 KB
Volume
54
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

Robust and straightforward methods are described for the first syntheses of highly pure ^13^C‐ and ^14^C‐labelled L‐5‐benzylhydantoin (L‐BH) and L‐5‐indolylmethylhydantoin (L‐IMH) by cyclizing the amino acids L‐phenylalanine and L‐tryptophan, respectively, with potassium cyanate. [3‐^13^C]‐L‐phenylalanine was used to prepare [6‐^13^C]‐L‐BH and [indole‐2‐^13^C]‐L‐tryptophan was used to prepare [indole‐2‐^13^C]‐L‐IMH, which we required for solid‐state NMR experiments with a hydantoin transport protein. The successful incorporation and integrity of the ^13^C labels was confirmed by solution‐state NMR spectroscopy. [^14^C]Potassium cyanate was used to prepare [2‐^14^C]‐L‐BH and [2‐^14^C]‐L‐IMH, which we required for transport assays with the protein. Copyright © 2010 John Wiley & Sons, Ltd.

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