title: 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.
abstract: 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.
authors.affiliation: Department of Chemistry, Warsaw University, Pasteura 1, Warszawa 02-093, Poland. atemer@chem.uw.edu.pl
authors.forename: Andrzej
authors.initials: A
authors.lastname: Temeriusz
authors.forename: Magdalena
authors.initials: M
authors.lastname: Rowińska
authors.forename: Katarzyna
authors.initials: K
authors.lastname: Paradowska
authors.forename: Iwona
authors.initials: I
authors.lastname: Wawer
mesh_terms: 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
chemical_list: D000596:Amino Acids; D002247:Carbon Isotopes; D004151:Dipeptides; D005960:Glucosides; D006001:Glycoconjugates; D011522:Protons; D010072:Oxamic Acid; C008728:oxamide