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Preparation of multi-labelled urocanic acids with 2H, 13C and 15N

✍ Scribed by Takashi Furuta; Motofusa Katayama; Hiromi Shibasaki; Yasuji Kasuya

Publisher
John Wiley and Sons
Year
1992
Tongue
French
Weight
297 KB
Volume
31
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

Two types of multi‐labelled urocanic acids with stable isotopes, i.e., [3‐^2^H,1′,3′‐^15^N~2~]urocanic acid and [2,3,5′‐^2^H~3~,2′‐^13^C,1′,3′‐^15^N~2~]urocanic acid were synthesized by the enzymatic reaction of DL‐[3,3‐^2^H~2~,1′,3′‐^15^N~2~]histidine or DL‐[2,3,3,5′‐^2^H~4~,2′‐^13^C,1′,3′‐^15^N~2~]histidine with histidine ammonia‐lyase (Pseudomonas fluorescens) at pH 9.0. The reaction of DL‐[2,3,3,5′‐^2^H~4~,2′‐^13^C,1′,3′‐^15^N~2~]histidine was achieved in D~2~O buffer system (pD 9.0) to avoid the enzyme‐catalyzed hydrogen exchange at C‐5′ of the imidazole ring. The isotopic purities were demonstrated to be 94 atom%, based upon the ion intensities in the region of the molecular ions of respective gas chromatographic derivatives measured by GC‐MS.

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