Synthesis and solid state 13C and 1H NMR analysis of new oxamide derivatives of methyl 2-amino-2-deoxy-alpha-D-glucopyranoside and ester of amino acids or dipeptides.
The syntheses of new oxamide derivatives of methyl 2-amino-2-deoxy-alpha-D-glucopyranoside and amino acid or peptide esters are presented. The reaction of methyl 3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-alpha-D-glucopyranoside and oxalyl chloride gave N-(methyl 3,4,6-tri-O-acetyl-2-deoxy-alpha-D-glucopyranosid-2-yl) oxamic acid chloride which on reaction with the ester of Gly, L-Ala, L-Phe, GlyGly, Gly-L-Phe and Gly-L-Ala afforded N-(methyl 3,4,6-tri-O-acetyl-2-deoxy-alpha-D-glucopyranosid-2-yl), N'-oxalyl-amino acid or dipeptide esters. The structure of the oxamides was studied using 1H, 13C NMR in solution and solid state.
Temeriusz
Andrzej
A
Department of Chemistry, Warsaw University, Pasteura 1, Warszawa 02-093, Poland. atemer@chem.uw.edu.pl
Rowińska
Magdalena
M
Paradowska
Katarzyna
K
Wawer
Iwona
I
D000596:Amino Acids / Q000737:chemistry; D002247:Carbon Isotopes; D004151:Dipeptides / Q000737:chemistry; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry; D006001:Glycoconjugates / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D010072:Oxamic Acid / Q000031:analogs & derivatives* / Q000737:chemistry*; D011522:Protons
D000596:Amino Acids; D002247:Carbon Isotopes; D004151:Dipeptides; D005960:Glucosides; D006001:Glycoconjugates; D011522:Protons; D010072:Oxamic Acid; C008728:oxamide