Studies of the Stability of Some Amino Acid Carbamates in Neutral Aqueous Solution

✍ Scribed by A.J. Davis; P. Obrien; P.B. Nunn

• Publisher: Elsevier Science
• Year: 1993
• Tongue: English
• Weight: 439 KB
• Volume: 21
• Category: Article
• ISSN: 0045-2068
• DOI: 10.1006/bioo.1993.1026

✦ Synopsis

The formation of carbamates by the amino acids L-cysteine, DL- (\alpha, \tau)-diaminobutyric acid, DL- (\alpha, \beta)-diaminopropionic acid, L-histidine, DL- (\alpha)-amino- (\beta)-methylaminopropionic acid and the dipeptide glycylglycine has been studied by ({ }^{1} \mathrm{H}) NMR spectroscopy in (\mathrm{D}{2} \mathrm{O}) and, in some cases, in (\mathrm{H}{2} \mathrm{O}). Values of the binding constants for (\mathrm{CO}{2}) to the free amine function ( (\mathrm{p} K{\mathrm{c}}) ) have been determined. For the diamino acids NMR spectroscopy allows the determination of the stability of the (\alpha) - and (\omega)-isomers. The results are used to comment on the likely extent of formation of carbamates from these amino acids in vivo. (c 1993) Academic Press. Inc.