These tools will no longer be maintained as of December 31, 2024. Archived website can be found here. PubMed4Hh GitHub repository can be found here. Contact NLM Customer Service if you have questions.
Pubmed for Handhelds
PUBMED FOR HANDHELDS
Search MEDLINE/PubMed
Title: An alternative synthesis of 4-deoxy-4-fluoro-D-glucose and its transport in the human erythrocyte. Author: Lopes DP, Taylor NF. Journal: Carbohydr Res; 1979 Aug; 73():125-34. PubMed ID: 476722. Abstract: Treatment of methyl 4-O-mesy-alpha-D-galactopyranoside with benzyl bromide in N,N-dimethylformamide in the presence of silver oxide yielded methyl 2,3,6-tri-O-benzyl-4-O-mesyl-alpha-D-galactopyranoside which with tert-butylammonium fluoride at reflux underwent nucleophilic displacement to give methyl 2,3,6-tri-O-benzyl-4-deoxy-4-fluoro-alpha-D-glucopyranoside. This compound on hydrogenolysis provided crystalline methyl 4-deoxy-4-fluoro-alpha-D-glucopyranoside (9). The structure of 9 was established by its conversion to the 2,3,6-tri-O-acetyl derivative and by n.m.r. and m.s. analysis. Acid hydrolysis of 9 gave 4-deoxy-4-fluoro-D-glucose (1). A modification of an established synthesis of 4-deoxy-D-xylo-hexose (2) from methyl 2,3,6-tri-O-benzoyl-alpha-D-galactopyranoside is described. A systematic comparison was made of the transport parameters (Kx and Vmax) of D-glucose, 2, and 1 in human erythrocytes. The Kx values observed for the above sugars are: 4.0mM, 4.5mM, and 4.6mM, respectively. These results indicate that O-4 in beta-D-glucopyranose is not involved in hydrogen bonding to the carrier protein associated with the transport of D-glucose in the erythrocyte.[Abstract] [Full Text] [Related] [New Search]