Deoxyhydroxyamino analogs of sugars: derivatives of methyl 2,3-dideoxy-2-hydroxyamino-α-d-arabino- and -lyxo-hexopyranosides
1991; Elsevier BV; Volume: 212; Linguagem: Inglês
10.1016/0008-6215(91)84046-h
ISSN1873-426X
AutoresJean M. J. Tronchet, N. Bizzozero, Martina Zsély, Françoise Barbalat‐Rey, Naz Dolatshahi, Gérald Bernardinelli, Michel Geoffroy,
Tópico(s)Polyamine Metabolism and Applications
ResumoN-Substituted hydroxylamines reacted both regio- and stereo-specifically with ethyl 2,3-dideoxy-α-d-glycero-hex-2-enopyranosid-4-ulose (1) to give N-substituted ethyl 2,3-dideoxy-2-hydroxyamino-α-d-threo-hexopyranosid-4-uloses (2–7), whereas O-methylhydroxylamine gave a mixture of O-methyloximes (8–10), including the product of both stereospecific conjugate addition and oximation (10). Sodium borohydride reduction of ethyl 2,3-dideoxy-2-(N-hydroxy-N-methylamino)- and 2,3-dideoxy-2-(N-hydroxy-N-isopropylamino)α-d-threo-hexopyranosid-4-uloses proceeded stereoselectively, and the major product had the α-d-arabino configuration. The conformations of these compounds were established using n.m.r. spectroscopy and X-ray diffraction for 3 and 19. The major interest of these deoxyhydroxyamino sugars was their easy oxidation into spin-labelled sugar analogs whose conformation could be studied by e.s.r. spectroscopy.
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