Guanosine diphosphate fucose

L-Fucose, 6-deoxy-L-galaclose a component of the blood-group sutetances A, B and O and of various oligosaccharides in human milk, seaweed, plant mucilages. Af, 164, m.p. (a-foim) 140 C, [a] -153 -76 (c = 9). It is also found in various glycosides and antibiotics. Some of the latter also contain D-fu-cose. l-F. is synthesized as its activated derivative, guanosine diphosphate fucose, from GDP-n-mannose by dehydrogenation, isomerization and reduction. 

Defect in transport or production of guanosine diphosphate L-fucose. Without the carbohydrate L-fucose, interaction of neutrophils with P- and E-selectins on endofiielial cells is affected. 

Guanosine diphosphate Mannose Synthesis of L-fucose, D-rhamnose and 6-deoxy hexoses... 

Fig. 20.1. Abbreviated scheme of the synthesis of a diantennary N-glycan. Fucose modification has been omitted. 20.1, Phosphomannomutase 2 (PMM2) 20.2, phosphoman-nose isomerase (PMI) 20.3, glucosyltransferase I (GT I) 20.4, mannosyltransferase VI (MT VI) 20.5, dolichol phosphate-mannose synthase-1 (DPM synthase-1) 20.5, N-acet-ylglucosaminyltransferase II (GnT II) 20.7, glucosidase I (G I) GDP, guanosine diphosphate Marly mannose GlcNACy N-acetylglucosamine Do/, dolichol P, phosphate G/c, glucose Gal galactose SiUy sialic acid. Dotted arrow indicates multiple steps...

L-Fucose, one of the eight essential monosaccharides (Section 25.7), is biosynthesized from GDP-o-mannose by the following three-step reaction sequence, where GDP = guanosine diphosphate (a ribonucleoside diphosphate Section 28.1) ... 

D-Mannose and L-fucose are related biogenetically and are transferred from their corresponding guanosine diphosphate-activated donors [57] by the corresponding transferases. GDP-Man constitutes an a-phosphate whereas in GDP-Fuc the diphosphate bridge is P-linked to the fucose unit. 

Cai, S, Stroud, M R, Hakomori, S, Toyokuni, T, Synthesis of carbocyclic analogs of guanosine 5 -(beta-L-fucopyranosyl diphosphate) (GDP-fucose) as potential inhibitors of fucosyltransferases, J. Org. Chem., 57, 6693-6696, 1992. 

L-fucose, D-rhamnose GDP-D-mannuronic acid GDP-4-keto-6-deoxy-D-mannose P, P -Diguanosine tetraphosphate P, P -Diguanosine triphosphate Guanosine tetraphosphate Cytidine diphosphate-X CDP-D-glucose CDP-L-ribitol... 

Kornfeld, R.H. Givsburg, V. Control of Synthesis of Guanosine 5 -Diphosphate D-Mannose and Guanosine 5 -Diphosphate L-Fucose in Bacteria. Biochim. Biophys. Acta 1966, 117, 79 87. 

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