[Synthesis of oligosaccharides related to HNK-1 antigen. 2. Synthesis of 3'''-O-(3-O-sulfo-beta-D-glucuronopyranosyl)-lacto-N-neotetrao se beta-propylglycoside].
A derivative of allyl 3"-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-beta-lactoside with a free OH group at C-4GlcNAc was glycosylated with trichloroacetimidate of selectively protected GlcA(beta 1-->3)Gal alpha disaccharide in dichloromethane in the presence of trimethylsilyl triflate resulting in a pentasaccharide product with an 82% yield. This product was converted to monohydroxy derivative with a free OH group at C-3GlcA via the formation and the subsequent opening of the 6,3-lactone ring in the glucuronic acid residue. The 3"'-O-sulfation of the monohydroxy derivative, the removal of the protective groups, and the reduction of the allyl aglycon yielded the pentasaccharide propyl glycoside NaSO3-3GlcA(beta 1-->3)Gal(beta 1-->4)GlcNAc(beta 1-->3)Gal(beta 1-->4)Glc beta-Opr comprising the oligosaccharide chain of the SGGL-1 glycolipid, which is recognized by HNK-1 antibodies. NaSO3-3GlcA(beta 1--> 3)Gal beta OAll, GlcA(beta 1-->3)Gal(beta 1-->4)GlcNAc(beta 1-->3)Gal(beta 1-->4)Glc beta-OPr and GlcA(beta 1-->3)Gal beta OAll were synthesized in a similar way.
Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia.
L O
LO
Kononov
A V
AV
Kornilov
A A
AA
Sherman
E V
EV
Zyrianov
G V
GV
Zatonskiĭ
A S
AS
Shashkov
N E
NE
Nifant'ev
D018959:CD57 Antigens / Q000737:chemistry*; D002240:Carbohydrate Sequence; D005915:Globosides / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D008752:Methylene Chloride; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D014297:Trimethylsilyl Compounds; D014574:Uronic Acids / Q000737:chemistry
C115476:3'''-O-(3-O-sulfoglucuronopyranosyl)-lacto-N-neotetraose propylglycoside; D018959:CD57 Antigens; D005915:Globosides; D006027:Glycosides; D009844:Oligosaccharides; D014297:Trimethylsilyl Compounds; D014574:Uronic Acids; C063678:3-sulfoglucuronyl-lacto-N-neotetraosylceramide; D008752:Methylene Chloride
Sintez oligosakharidov, rodstvennykh antigenu HNK-1. 2. Sintez beta-propilglikozida 3'''-O-sulfo-beta-D-gliukuronopiranozil)-lakto- N-neotetraozy.