Transformation of quercitols into 4-methylenecyclohex-5-ene-1,2,3-triol derivatives, precursors for the chemical chaperones N-octyl-4-epi-β-valienamine (NOEV) and N-octyl-β-valienamine (NOV)
2011; Elsevier BV; Volume: 21; Issue: 23 Linguagem: Inglês
10.1016/j.bmcl.2011.09.067
ISSN1464-3405
AutoresShin‐ichi Kuno, Atsushi Takahashi, Seiichiro Ogawa,
Tópico(s)Protein Structure and Dynamics
Resumo(+)-proto-Quercitol (1) and (−)-vibo-quercitol (2), both of which could be readily prepared by the bioconversion of myo-inositol, were successfully converted into the corresponding 4-methylenecyclohex-5-ene-1,2,3-triol derivatives. These compounds were demonstrated to be suitable precursors, preserving their configurations, for bioactive carba-aminosugars such as the potent chemical chaperone drug candidates, N-octyl-4-epi-β-valienamine (NOEV, 3) and N-octyl-β-valienamine (NOV, 4).
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