CARBON 13 NUCLEAR MAGNETIC RESONANCE STUDIES ON FORMALDEHYDE REACTIONS WITH POLYFUNCTIONAL AMINO‐ACIDS
- 1 April 1981
- journal article
- research article
- Published by Wiley in International Journal of Peptide and Protein Research
- Vol. 17 (4) , 501-507
- https://doi.org/10.1111/j.1399-3011.1981.tb02020.x
Abstract
Addition and condensation reactions of formaldehyde with poly functional amino‐acids and their Nα‐acetyl derivatives have been studied in neutral or mildly acid solutions using 13C n.m.r.The first addition reaction, giving hydroxymethyls, is fast and incomplete with the amine, guanidyl, hydroxyl, indole and imidazole groups of the side chains, fast and complete with the sulfhydryl group, slow and complete with the amide group.For asparagine, threonine, histidine and tryptophan, the Nα‐hydroxymethyl condenses with the basic group of the side chain to give a cyclic compound. In the case of cysteine, it is the S‐hydroxymethyl which condenses with the α‐amino group.The value of the chemical shifts of the hydroxymethyls and of the methylene bondings will be of help in the study of the reactions of formaldehyde with proteins.Keywords
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