Synthesis of the repeating unit of the teichoic acid isolated from the cell wall of bacillus subtilis VAR. niger WM |
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Authors: | Tomoya Ogawa Kiyoaki Katano Masanao Matsui |
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Affiliation: | The Institute of Physical and Chemical Research, Wako-shi, Saitama, 351 Japan |
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Abstract: | Stereocontrolled synthesis of 1-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,3-O-isopropylidene-D-glycerol (6) was achieved in good yield by use of the modified, orthoester method. Compound 6 was then transformed into 1-deoxy-3-O-phosphono-D-glycerol-1-yl β-D-glucopyranoside (1), identical with the repeating unit of the teichoic acid isolated from the cell wall of Bacillus subtilis var. niger WM, in a regio-controlled way, unambiguous evidence for the assignment of the stereochemistry of the natural product being provided by the 13C-n.m.r. data for 1 and its L-glycerol-1-yl isomer. |
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Keywords: | To whom enquiries should be addressed. |
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