Trehaloses carba

The carba-trehaloses are carbocyclic analogs of trehalose, in which one or both of the D-glucopyranose units is (are) replaced with D-carba-glucopy-ranose, and may be expected to act as a substrate analog or an inhibitor of... 

Among the eight possible diastereoisomers of carba-trehalose of type C, only that isomer having the same configuration as the natural trehalose was found to be a substrate of certain maltases or trehalases. ... 

Such carba-disaccharides as validoxylamines A and B were synthesized as intermediary compounds in the total synthesis of validamycin antibiotics. Carba-disaccharides related to maltose, isomaltose, cellobiose, the trehaloses, and trehalosamine modifications have also been synthesized. 

In a further molecular mechanics study (MM3), the energy surfaces of a,a-, a,p-, and P,P-trehalose were compared with those of the corresponding 2-(6-methyltetrahydropyran-2-yloxy)-6-methyltetrahydropyrans and 5a-carba trehaloses it was concluded that the exo-anomeric effect plays an important role and that linkage-type (a or p) is more important than the presence or absence of exocyclic substituents in detomining disaccharide conformations. The preferred solution conformations of eight (l- )-C-linked disaccharides, such as compounds 13, have been determined on the basis of vicinal H- H coupling constants, and conformational similarities between... 

In the area of carba-disaccharides, the synthesis of dicarba-a,a-trehalose, togedier widi the analogues 110a and 111 have been reported as potential trehalase inhibition. ... 

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