title: Bicyclic amino acid-carbohydrate-conjugates as conformationally restricted hydroxyethylamine (HEA) transition-state isosteres.
abstract: This communication describes a general synthetic route to bicyclic amino acid-carbohydrate-conjugates, which would be useful as conformationally restricted hydroxyethylamine (HEA) transition-state isosteres. The synthesis was achieved in 12 steps starting from D-glucose. The striking features of this system are the bicyclic rigid core displaying an α-amino acid side chain and hydroxyethylamine moiety--both of which would be potentially important for receptor interactions, leading to various biomedical responses, as described in the literature. Crystal structure investigation suggested extensive intermolecular hydrogen-bonding interactions in this system, involving the backbone amide and hydroxyl groups.
authors.affiliation: Division of Organic Chemistry, National Chemical Laboratory, Dr Homi Bhabha Road, Pune, 411 008, India.
authors.forename: Sangram S
authors.initials: SS
authors.lastname: Kale
authors.forename: Sanjay T
authors.initials: ST
authors.lastname: Chavan
authors.forename: Sushma G
authors.initials: SG
authors.lastname: Sabharwal
authors.forename: Vedavati G
authors.initials: VG
authors.lastname: Puranik
authors.forename: Gangadhar J
authors.initials: GJ
authors.lastname: Sanjayan
mesh_terms: D000598:Amino Acids, Cyclic / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D018360:Crystallography, X-Ray; D004983:Ethanolamines / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D000598:Amino Acids, Cyclic; D002241:Carbohydrates; D004983:Ethanolamines