Synthesis and characterisation of N-glycosyl amines from the reaction between 4,6-O-benzylidene-D-glucopyranose and substituted aromatic amines and also between 2-(o-aminophenyl)benzimidazole and pentoses or hexoses.
Twelve N-glycosyl amines were synthesised using 4,6-O-benzylidene-D-glucopyranose and different substituted aromatic amines, including some diamines that resulted in bis-glycosyl amines. Another set of six N-glycosyl amines was synthesised using different hexoses and pentoses and 2-(o-aminophenyl)benzimidazole. All compounds were isolated as solid products and purified, their elemental compositions were established, and these were characterised by NMR (1H and 13C), UV-Vis, and FTIR spectroscopy, by FAB mass spectrometry (molecular-ion peaks gave molecular weights), and by their optical rotations. While the protected saccharide, 4,6-O-benzylidene-D-glucopyranose, exists as a mixture of beta and alpha anomers in solution, the corresponding N-glycosyl amines were of only the beta anomeric form as determined by NMR and FTIR spectroscopy. On the other hand, N-glycosyl amines synthesised from 2-(o-aminophenyl)benzimidazole prefer the alpha anomeric form, and in two cases a mixture of both the beta and the alpha anomers were observed. The trends observed in the chemical shifts were compared among different products.
Das
T M
TM
Bioinorganic Laboratory, Department of Chemistry, Indian Institute of Technology Bombay, Powai, 400 076, Mumbai, India.
Rao
C P
CP
Kolehmainen
E
E
D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry*; D001562:Benzimidazoles / Q000737:chemistry*; D002240:Carbohydrate Sequence; D005947:Glucose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*; D006031:Glycosylation; D006601:Hexoses / Q000737:chemistry*; D006860:Hydrogen Bonding; D008969:Molecular Sequence Data; D019906:Nuclear Magnetic Resonance, Biomolecular; D010429:Pentoses / Q000737:chemistry*; D011084:Polycyclic Aromatic Hydrocarbons / Q000737:chemistry
C412329:2-(2'-aminophenyl)benzimidazole; C438444:4,6-O-benzylidene-D-glucopyranose; D000588:Amines; D001562:Benzimidazoles; D006601:Hexoses; D010429:Pentoses; D011084:Polycyclic Aromatic Hydrocarbons; D005947:Glucose