Characterization of the 4-Acetamido-4,6-dideoxyhexoses from Escherichia coli Strains
Year: 1973
Type: article
Abstract: TDP-sugar compounds containing unusual acetamido sugars were previously isolated from Escherichia coli strains and synthesized enzymatic&y.Data which led to the characterization of these sugars as 4-acetamido-4,6-dideoxy-D-glucose and 4-acetamido-4,6-dideoxy-D-galactose are reported in the present paper.In 1959, Okazaki et al. (I) reported the occurrence of unusual thymidine compounds in microorganisms and Strominger and Scott (2) reported the isolation of thymidine diphosphosugar compounds.These compounds were isolated from Escher&a coli Y-10 and were called TDP-X, TDP-Y, and TDP-Z.Then Okazaki et al. (3) isolated another thymidine diphosphosugar compound, TDP-X2, from lj:. coli B. Since these initial discoveries, several other groups of investigators have shown that other thymidine diphosphosugars occur in various microorganisms.Subsequent study (4, 5) revealed that TDP-Y is TDPI-keto-6-deoxy+glucose (an intermediate in TDP-L-rhamnose synthesis) and that TDP-Z is a mixture of TDP-D-fucose and TDP-Bdeoxy-n-glucose.The sugars X and XZ of TDP-X and TDP-X2were shown to contain an N-acetyl group, and some other chemical properties were described (6, 7).Both TDP-X and TDP-X2 have been synthesized enzymatically (8-11).This report is concerned with a study of the structure of the sugar X isolated from E. coli Y-10 and the enzymatically synthesized sugars X and X2.A preliminary report of the identification of the sugar X has appeared (10).MATERIALS AND METHODS Biochemicals and Enzymes-[14C]Threonine (0.88 mCi per mmole) was obtained from Volk Radiochemical Co., Skokie, Ill.N-Acetylthreonine and n-allothreonine were obtained from Cycle Chemical Co., Los Angeles, Calif.Crystalline formyltetrahydrofolate synthetase (12) and tetrahydrofolic acid (13) were gifts
Source: Journal of Biological Chemistry
Authors: David N. Dietzler, Jack L. Strominger
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $3,430
OpenAlex ID: W1564368740