1,3-Parallel O/ /O interactions in acyclic carbohydrates: the crystal and molecular structures of meso-d-glycero-l-altro-heptitol and the monohydrate, meso-d-glycero-l-ido-heptitol, and meso-d-glycero-l-altro-heptitol and d-glycero-l-galacto-heptitol heptaacetates

Substrate specificity of sheep liver sorbitol dehydrogenase

“…Polyols which were unavailable from commercial sourcesincluding the hexitols (meso)-allitol, -glucitol (-gulitol), -mannitol, -altritol (-talitol), -altritol (-talitol) and -iditol, all the heptitols investigated, 1,2,3-heptanetriol (70 % -threo, 30 % -erythro), -threo-1,2,3-octanetriol, -erythro-1,2,3-octanetriol, 1,2,7,8-octanetetrol, 6-deoxy-6-nitro--iditol, 6-deoxy--mannitol,3-deoxysorbitol,6-deoxysorbitol, 1,6-dideoxysorbitol, 1-deoxy-1-aminosorbitol, N-methyl-N-octanoyl-1-deoxy-1-amino-sorbitol and various nitro derivatives of heptitols -were synthesized (see [2,3,[17][18][19] and references cited therein for preparation of polyols and derivatives). The compounds synthesized were, on the basis of "$C NMR, found to be 98 % pure.…”

“…The existence of a hydrophobic site in the vicinity of the catalytic metal complex in SDH is indicated by the enzyme structure model [15], and nonpolar interactions appear involved also in the binding of reversible inhibitors [14] and affinity labelling reagents [46,47]. Inspection of the three-dimensional conformations of the polyols investigated [2,18,19] raises the possibility that the nonpolar backbone of various polyols is involved in hydrophobic interactions with the enzyme. For the polyols with the favourable cis-2,4 dihydroxy configuration (-xylo, -xylo, -ribo ; Figure 2), an intramolecular 2,4 parallel O\ \O interaction induces bending of the carbon chain at C2, stabilizing the energetically most stable (bent chain) conformation with a nonpolar backbone.…”