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Synthesis of oxygen‐18 isotope labeled amino acids and dipeptides and its effects on carbon‐13 NMR
Author(s) -
Ponnusamy E.,
Jones C. C.,
Fiat D.
Publication year - 1987
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.2580240707
Subject(s) - chemistry , amino acid , hydrolysis , glycine , alanine , carbon fibers , kinetic isotope effect , acetonitrile , carboxylic acid , carbon 13 , isotopes of carbon , organic chemistry , medicinal chemistry , deuterium , biochemistry , materials science , physics , quantum mechanics , composite number , total organic carbon , composite material
Oxygen‐18 isotope labeled at the carboxyl group of glycine, L‐alanine and L‐proline were synthesized by acid catalyzed exchange or acid hydrolysis of respective methyl ester derivatives of amino acids in HC1/H 2 18 O. Quantitative enrichment of glycine was achieved by the acid hydrolysis of amino acetonitrile in H 2 18 O. In order to conserve the isotopic enrichment [ 18 O] dipeptides were synthesized by solid phase method. [ 18 O] isotope effects on [ 13 C] NMR of carboxylic carbon of amino acids and carbonyl carbon of peptides was observed. The [ 18 O] isotopic shifts observed for the carboxylic carbon of singly and doubly [ 18 O] labeled amino acids showed that the [ 18 O] isotope effect is additive.