Idose 2,6-diamino-2,6-dideoxy

When the paromobiosamine fraction is W-benzoylated and then hydrolyzed with dilute acid, D-ribose is one of the products. More-vigorous hydrolysis destroys the D-ribose but yields a diaminodideoxyhexose which was called paromose. A study of the products of periodate oxidation of paromose, of its di-W-acetyl derivative, and of the borohydride reduction product of the latter, revealed that paromose is a 2,6-diamino-2,6-di-deoxyhexose. In a preliminary report, Haskell and Hanessian have presented degradative evidence which establishes the stereochemical structure of paromose as that of 2,6-diamino-2,6-dideoxy-L-idose (7). Their ingenious application of the degradation described by MacDonald and Fischer and by Hough and coworkers of the 1, l-bis(ethanesulfonyl) derivatives of aldoses enabled Haskell and Hanessian to obtain, from iV,fV -diacetylparomose diethyl dithioacetal, a product which they identi-... 

C23H4 N 0 3 614.649 Aminoglycoside antibiotic. Prod, by Streptomyces fradiae and other spp. Clinically used broad-spectrum antibiotic. Amorph. [a]o +83 (c, 1 in 0.2M H2SO4). Log P -9.03 (uncertain value) (calc). Indefinite Mp. Hydrol. - Neomycin A, D-ribose and 2,6-diamino-2,6-dideoxy-L-idose. 

Periodate oxidation of suitably protected derivatives of paromomycin and neomycin B, followed by base-catalysed jS-elimination, yielded 5-O-jS-D-ribo-furanosyl- and 5-0-jS-neobiosaminyl-2-deoxystreptamine derivatives, respectively (see also Vol. 8, p. 136). Acidic hydrolysis of penta-A-acetylparomo-mycin liberated 2-amino-2-deoxy-D-glucose, 2-deoxystreptamine, neosamine B (2,6-diamino-2,6-dideoxy-L-idose), and o-ribose, which were separated on a cation-exchange resin. (2-Amino-2-deoxy- and 6-amino-6-deoxy-a-D-gluco-pyranosyl)-2,5-dideoxystreptamine have been synthesized and shown to possess antibacterial activities. ... 

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