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A convenient synthesis of creatine‐ 15 N from glycine‐ 15 N via sarcosine‐ 15 N
Author(s) -
Greenaway W.,
Whatley F. R.
Publication year - 1978
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.2580140417
Subject(s) - sarcosine , chemistry , glycine , creatine , aqueous solution , betaine , hydrolysis , ammonium , inorganic chemistry , amino acid , organic chemistry , biochemistry
The preparation of creatine‐ 15 N monohydrate from glycine‐15N with the isolation of sarcosine‐15N as an intermediate is described. Glycine‐15N (97.3 atom% 15N) is converted to benzenesulphonyl glycine‐15N, which is methylated to give benzenesulphonyl sarcosine‐15N. The latter is hydrolysed to sarcosine‐15N, which is isolated by ion exchange chromatography. Sarcosine‐15N is converted to creatine‐15N monohydrate by reaction with cyanamide in aqueous solution in the presence of sodium chloride and catalytic amounts of ammonium hydroxide‐14N. The creatine‐15N monohydrate precipitated from the above reaction mix is recrystallized from boiling water. The yield of sarcosine‐15N from glycine‐15N is 78% of theory and that of recrystallized creatine‐15N monohydrate from glycine‐15N is 59% of theory.