Convenient chemoenzymatic synthesis of beta-purine-diphosphate sugars (GDP-fucose-analogues).
A series of peracetylated beta-sugar-1-phosphates with L-fuco configuration are efficiently prepared chemically and coupled in high yields to purine monophosphate bases via imidazolide activation. The resulting purine diphosphate sugars are deacetylated completely by a mild treatment with commercial acetylesterase (EC 3.1.1.6) to give donor-substrates for fucosyl-transferases.
Baisch
G
G
Central Research Laboratories CIBA AG, Basle, Switzerland.
Ohrlein
R
R
D000115:Acetylesterase / Q000737:chemistry*; D006154:Guanosine Diphosphate Fucose / Q000031:analogs & derivatives*; D009682:Magnetic Resonance Spectroscopy; D013403:Sugar Phosphates / Q000138:chemical synthesis*
D013403:Sugar Phosphates; D006154:Guanosine Diphosphate Fucose; D000115:Acetylesterase