196876-45-6Relevant articles and documents
Pseudosugars, 40: Synthesis of ether- and imino-linked octyl N-acetyl- 5a'-carba-β-lactosaminides and -isolactosaminides: Acceptor substrates for α-(1→3/4)-fucosyltransferase, and enzymatic synthesis of 5a'- carbatrisaccharides
Ogawa, Seiichiro,Matsunaga, Naoki,Li, Hong,Palcic, Monica M.
, p. 631 - 642 (2007/10/03)
Synthesis of ether-linked octyl 5a'-carba-β-lactosaminide 3 and - isolactosaminide 5 was carried out in seven steps, starting from the coupling products of 1,2-anhydro-5a-carba-β-D-mannopyranose derivative 7, and the oxide anions generated from the octyl N-acetyl-β-D-glucosaminide derivatives 13 and 16, respectively, under basic conditions. The 5a-carba-α-D- mannopyranose residues of the coupling products 17 and 26 were transformed into the β-D-gluco configuration through epimerization of the respective 2'- oxo derivatives 19 and 28, and selective reduction, and then into the β-D- galacto configuration by direct nucleophilic substitution of their 4',6'- dimesylates 23 and 31 with an acetate ion. Biological assay has shown that 3 is an acceptor substrate for human-milk α-(1→3/4)-fucosyltransferase and, interestingly, 5 is not. In addition, the imino-linked congeners 4 and 6 have been synthesized by coupling of the 4-amino-4-deoxy- and 3-amino-3-deoxy derivatives 37 and 41 of octyl N-acetyl-β-D-glucosaminide, and the carba- sugar epoxide 8, respectively, and subsequent deprotection. Compound 4 is a substrate while 6 is neither a substrate nor an inhibitor for fucosyltransferase. Small-scale enzymatic synthesis was carried out by treatment of 3 and 4 with GDP-fucose and milk fucosyltransferase, which resulted in conversion into the corresponding trisaccharides 47 and 48, respectively.
Generation of molecular diversity on N-acetyllactosamine via O-cyanomethyl ethers
Malet, Carles,Hindsgaul, Ole
, p. 51 - 65 (2007/10/03)
The ability to generate molecular diversity around a natural carbohydrate ligand taking advantage of the rich chemistry of the nitrile functional group was demonstrated by synthesizing 24 derivatives of N-acetyllactosamine (LacNAc). The disaccharides prepared carried carboxymethyl, amidinomethyl, aminoethyl, and carbamoylmethyl substituents projecting from each of the six OH groups. The resulting LacNAc derivatives present new structural features with either negatively charged, positively charged, or polar-neutral small substituents sampling the entire periphery of the molecule. These new derivatives should be useful probes for studying carbohydrate-protein interactions in general, and for designing inhibitors of N-acetyllactosamine-binding proteins in particular.
