Biomaterial Database

A total synthesis of hematoside, alpha-NeuGc-(2----3)-beta-Gal-(1----4)-beta-Glc-(1----1)-Cer. 1988

M Numata, and M Sugimoto, and S Shibayama, and T Ogawa

RIKEN (The Institute of Physical and Chemical Research), Saitama, Japan.

Methyl (5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5- dideoxy-D-glycero-beta-D-galacto-2-nonulopyranosyl chloride)onate, prepared from N-glycolyl-neuraminic acid, was used for the glycosylation of benzyl O-(2,6-di-O-benzyl-beta-D- galactopyranosyl)-(1----4)-2,3,6-tri-O-benzyl-beta-D-glucopyranoside to give benzyl O-[methyl (5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero- alpha- and beta-D-galacto-2-nonulopyranosyl)onate]-(2----3)-O-(2,6-di-O -benzyl-beta- D-galacto-pyranosyl)-(1----4)-2,3,6-tri-O-benzyl-beta-D-glucopyranoside, and a regioisomer. Compounds 9 and 13 were converted into the corresponding glycotriaosyl glycosyl donors which, upon coupling with (2S,3R,4E)-3-O-tert-butyldiphenylsilyl-2-N- tetracosanoylsphingenine, afforded completely protected hematoside and a stereoisomer 26, respectively. Deprotection of 22 and 26 completed the first total synthesis of both hematoside and a stereoisomer, beta-NeuGc-(2----3)-beta-Gal-(1----4)-beta-Glc-(1----1)-Cer.

UI	MeSH Term	Description	Entries
D007202	Indicators and Reagents	Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499)	Indicator,Reagent,Reagents,Indicators,Reagents and Indicators
D009682	Magnetic Resonance Spectroscopy	Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING).	In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
D009904	Optical Rotation	The rotation of linearly polarized light as it passes through various media.	Optical Activity,Activity, Optical,Rotation, Optical
D002236	Carbohydrate Conformation	The characteristic 3-dimensional shape of a carbohydrate.	Carbohydrate Linkage,Carbohydrate Conformations,Carbohydrate Linkages,Conformation, Carbohydrate,Conformations, Carbohydrate,Linkage, Carbohydrate,Linkages, Carbohydrate
D005679	G(M3) Ganglioside	A ganglioside present in abnormally large amounts in the brain and liver due to a deficient biosynthetic enzyme, G(M3):UDP-N-acetylgalactosaminyltransferase. Deficiency of this enzyme prevents the formation of G(M2) ganglioside from G(M3) ganglioside and is the cause of an anabolic sphingolipidosis.	Hematoside,Sialyllactosylceramide,Ganglioside GM3,II3NeuAcLacCer,Sialyl Lactosylceramide,GM3, Ganglioside,Lactosylceramide, Sialyl
D005732	Gangliosides	A subclass of ACIDIC GLYCOSPHINGOLIPIDS. They contain one or more sialic acid (N-ACETYLNEURAMINIC ACID) residues. Using the Svennerholm system of abbrevations, gangliosides are designated G for ganglioside, plus subscript M, D, or T for mono-, di-, or trisialo, respectively, the subscript letter being followed by a subscript arabic numeral to indicated sequence of migration in thin-layer chromatograms. (From Oxford Dictionary of Biochemistry and Molecular Biology, 1997)	Ganglioside,Sialoglycosphingolipids
D013237	Stereoisomerism	The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)	Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer