Cell wall mannan of the pathogenic yeast Candida krusei was prepared using the antibiotic Benanomicin A, which has a lectin-like function. The chemical structure of this molecule was found to be similar to that of mannan prepared from the same yeast by the conventional method using Fehling reagent. Only a few degradation products were detected when the mannan prepared using Fehling reagent was subjected to alkali treatment (β-elimination), but multiple α-1,2-linked oligosaccharides were detected when the mannan purified with Benanomicin A was treated with alkali. These results indicate that most of the O-linked sugar chains in mannan were lost under conventional conditions when exposed to the strongly alkaline Fehling reagent. In contrast, the O-glycosidic bond in mannan was not cleaved and the O-linked sugar chains were maintained and almost intact following treatment with the mild novel preparation method using Benanomicin A. Therefore, we argue that the new mannan preparation method using Benanomicin A is superior to conventional methods. In addition, our study suggests that some yeast mannans, whose overall structure has already been reported, may contain more O-linked sugar chains than previously recognized.

β-elimination, antibiotic, Cell wall mannan, Benanomicin A, Candida krusei, O-linked sugar

13C NMR data:
missing...

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

OC[C@H]1O[C@H](O)[C@@H](O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O)[C@@H](O)[C@@H]1O

666.579 g/mol (C₂₄H₄₂O₂₁)