Synthesis and conformational analysis of methyl 3-amino-2,3-dideoxyhexopyranosiduronic acids, new sugar amino acids, and their diglycotides.
The synthesis of methyl 3-azido- and 3-amino-2,3-dideoxyhexopyranosiduronic acids and their methyl esters with the -alpha,beta-D-arabino-, -alpha,beta-D-ribo, and -alpha,beta-L-lyxo configurations is presented. The conformations of the synthesized sugar amino acids and their precursors are discussed on the basis of 1H NMR data. The influence of the 5-carboxyl group on the pyranose ring conformation is assessed, and the bonding of the monosugar amino acids into dimeric glycotides, using conventional solution-phase peptide syntheses, is reported.
Tuwalska
Dorota
D
Faculty of Chemistry, University of Gdańsk, Sobieskiego 18, Pl-80-952 Gdańsk, Poland.
Sienkiewicz
Joanna
J
Liberek
Beata
B
D000107:Acetylation; D000606:Amino Sugars / Q000138:chemical synthesis*; D006603:Hexuronic Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
D000606:Amino Sugars; D006603:Hexuronic Acids