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Synthesis of [(1S)-(1,2,4/3,5)-2-amino-3,4-dihydroxy-5-(hydroxymethyl)-1-cyclohexyl] α-d-glucopyranoside

✍ Scribed by Seiichiro Ogawa; Tatsuhi Toyokuni; Yoshio Hattori; Taisuke Nose; Tetsuo Suami

Publisher
Elsevier Science
Year
1986
Tongue
English
Weight
469 KB
Volume
146
Category
Article
ISSN
0008-6215

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✦ Synopsis

As part of a study of the elucidation of biochemical and biological properties of pseudo-sugars', replacement of the hexopyranosyl residues of biologically active disaccharides with structurally related pseudo-sugars has been investigated. Trehalosamine* (1) is an aminoglycoside antibiotic3 produced by Streptomyces lavendulae. It is an cu,cu-(l+l)-linked disaccharide composed of D-glucose and 2-amino-2-deoxy-D-glucose. Three related compounds, the 3-amino-3-deoxy4 1 Treholosamlne A and 4-amino-4-deoxy isomers5, and 2-amino-2-deoxy-a-D-glucopyranosyl U-D-mannopyranoside6, have thus far been shown to possess antibacterial activity. The synthesis and biological activities of analogous disaccharides have been extensively studied by Baer and his co-workers7-9. Three types of pseudo-sugar analogues of trehalosamine may be considered: *Synthesis of Pseudo-trehalosamine and Related Pseudo-disaccharides. Part I.

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