Synthesis of Carbon-Backbone-Elongated GDP-L-Fucose Derivatives as Substrates for Fucosyltransferase-Catalysed Reactions
| العنوان: | Synthesis of Carbon-Backbone-Elongated GDP-L-Fucose Derivatives as Substrates for Fucosyltransferase-Catalysed Reactions |
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| المؤلفون: | Ole Hindsgaul, Thisbe K. Lindhorst, Claudia Bergemann, Christer Hällgren, Joachim Thiem, Andrej-Jakob Ott, Wilhelm V. Dahlhoff, Christian Vogel, Monica M. Palcic |
| المصدر: | Liebigs Annalen. 1997:601-612 |
| بيانات النشر: | Wiley, 1997. |
| سنة النشر: | 1997 |
| مصطلحات موضوعية: | chemistry.chemical_classification, Fucosyltransferase, biology, Stereochemistry, Organic Chemistry, Guanosine, Glycoside, General Chemistry, Fucose, Coupling reaction, Turn (biochemistry), chemistry.chemical_compound, chemistry, Wittig reaction, biology.protein, Swern oxidation, Physical and Theoretical Chemistry |
| الوصف: | Starting from the 6-O-tert-butyldimethysilyl-2,3;4,5-di-O-isopropylidene-D-galactose diethyl dithioacetal (4) and proceeding through a Wittig reaction and Swern oxidation, a series of L-fucose analogues, which unlike the normal L-fucose possess an extended alkyl-chain at C-5, can be produced. The elongated carbon backbone in the L-fucitols (22–25) as well as in the L-fucose derivatives (30–33) increases the hydrophobic nature of the sugar molecule, promoting liquid-crystalline properties in both series. The further derivatization of the L-fucose analogues 30, 31 leads to the corresponding β-L-galacto-deco- and dodeco-pyranosyl phosphates 46, 47 and, in turn, to the respective pyranosyl guanosine 5-diphosphates 48, 49. The reaction of the β-L-galactopyranosyl guanosine 5-diphosphate 48 with 8-methoxycarbonyloctyl 2-acetamido-2-deoxy-4-O-(β-D-galactopyranosyl)-β-D-glucopyranoside (50) in the presence of a 3/4-α-fucosyltransferase furnished an O-glycosidic linkage of the α-L-galactopdecopyranose 30 at the 3-O-position of the N-acetyllactosamine glycoside 50. The chemo-enzymatic coupling reaction proves that the synthesized carbon-backbone-elongated L-galactopyranosyl guanosine 5-diphosphates are suitable substrates for the α-fucosyltransferases. |
| تدمد: | 1099-0690 0947-3440 |
| الوصول الحر: | https://explore.openaire.eu/search/publication?articleId=doi_________::991f709047c3ff3281dca776709cfb02Test https://doi.org/10.1002/jlac.199719970323Test |
| حقوق: | CLOSED |
| رقم الانضمام: | edsair.doi...........991f709047c3ff3281dca776709cfb02 |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 10990690 09473440 |
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