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Synthesis of ortho deuterated phenylisocyanate under mild conditions

✍ Scribed by M. A. Masson; J. R. Dormoy

Publisher
John Wiley and Sons
Year
1979
Tongue
French
Weight
193 KB
Volume
16
Category
Article
ISSN
0022-2135

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✦ Synopsis

A new method h a s been developed for t h e s y n t h e s i s of phenylisocyanate 2 -H through t h e u s e of a z i d o (tris dimethylamino) phosphonium hexa-2 fluorophosphate and benzoic a c i d 2-H. The product prepared is obtained with a high percentage of isotopic substitution, specificity of l a b e i and appreciable yield. 2 I -INTRODUCTION The method of Bergmann e t al. (1) w a s used by Abderhalden and Brockmann (2) and by Jensen and Evans (3) to determine the N-terminal group of a peptide or a protein by removal of only one residue. The identification of t h e N-terminal amino-acid w a s determined through t h e u s e of phenylis o c y a n a t e as t h e coupling reagent. Phenylisocyanate r e a c t s with t h e alpha amino groups a t pH=8 and 0°C. The phenylcarbamyl peptide obtained undergoes a cyclization a t 100°C for one hour in t h e presence of methanol or hydrochloric acid.

The application of Bergmann's method t o low quantities of proteins and peptides i s p o s s i b l e if labeled phenylisocyanate i s u s e d . Such an application led to t h e s y n t h e s i s of the ortho deuterated phenylisocyanate 2

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