Synthesis of new 2-C-(2,3:5,6-di-O-isopropylidene)-beta-D-mannofuranosyldithioacetate derivatives. 2005

Zaira J Dominguez, and Patrice Marchand, and Mihaela Gulea, and Serge Masson
Unidad de Servicios de Apoyo en Resoluciòn Analitica, Universidad Veracruzana. Xalapa Ver., Mexico.

Various new C-glycosides have been synthesized through the thioacylation reaction of different amines by a 2-C-mannofuranosyldithioacetate. Amino acids, di- and polyamines (putresceine, spermine, spermidine) and one amino alcohol were in particular used to generate glycothiopeptidic or precursors of "bola" structures.

UI MeSH Term Description Entries
D008358 Mannose A hexose or fermentable monosaccharide and isomer of glucose from manna, the ash Fraxinus ornus and related plants. (From Grant & Hackh's Chemical Dictionary, 5th ed & Random House Unabridged Dictionary, 2d ed) D-Mannose,Mannopyranose,Mannopyranoside,D Mannose
D010455 Peptides Members of the class of compounds composed of AMINO ACIDS joined together by peptide bonds between adjacent amino acids into linear, branched or cyclical structures. OLIGOPEPTIDES are composed of approximately 2-12 amino acids. Polypeptides are composed of approximately 13 or more amino acids. PROTEINS are considered to be larger versions of peptides that can form into complex structures such as ENZYMES and RECEPTORS. Peptide,Polypeptide,Polypeptides
D011073 Polyamines Amine compounds that consist of carbon chains or rings containing two or more primary amino groups. Polyamine
D002240 Carbohydrate Sequence The sequence of carbohydrates within POLYSACCHARIDES; GLYCOPROTEINS; and GLYCOLIPIDS. Carbohydrate Sequences,Sequence, Carbohydrate,Sequences, Carbohydrate
D004952 Esters Compounds derived from organic or inorganic acids in which at least one hydroxyl group is replaced by an –O-alkyl or another organic group. They can be represented by the structure formula RCOOR’ and are usually formed by the reaction between an acid and an alcohol with elimination of water. Ester
D006027 Glycosides Any compound that contains a constituent sugar, in which the hydroxyl group attached to the first carbon is substituted by an alcoholic, phenolic, or other group. They are named specifically for the sugar contained, such as glucoside (glucose), pentoside (pentose), fructoside (fructose), etc. Upon hydrolysis, a sugar and nonsugar component (aglycone) are formed. (From Dorland, 28th ed; From Miall's Dictionary of Chemistry, 5th ed) Glycoside
D006868 Hydrolysis The process of cleaving a chemical compound by the addition of a molecule of water.
D000215 Acylation The addition of an organic acid radical into a molecule.
D000588 Amines A group of compounds derived from ammonia by substituting organic radicals for the hydrogens. (From Grant & Hackh's Chemical Dictionary, 5th ed) Amine
D000596 Amino Acids Organic compounds that generally contain an amino (-NH2) and a carboxyl (-COOH) group. Twenty alpha-amino acids are the subunits which are polymerized to form proteins. Amino Acid,Acid, Amino,Acids, Amino

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