Structure of Melezitose

The establishment of the structure of turanose furnishes a firm basis for an eventual determination of the structure of melezitose. One can start with the assurance that the trisaccharide is 8-[a-v-glucopyranosyVy D-fructose < > n-glucopyranose this formula requires three further specifications. The first of these is an allocation of a ring to the fructose unit, the second is a decision between the a- and /S-forms for this unit, and the third is a similar decision between these forms for the right-hand D-glucopyranose unit. Decision on these three matters can be made readily if sucrose should ever be found to result from a partial hydrolysis of melezitose, because sucrose is almost certainly f)-v-fructo-... 

Hehre, Edward J., The Substituted-su-crose Structure of Melezitose, VIII, 277-290... 

One of the major points advanced by Kuhn and von Grundherr for the substituted-sucrose structure of melezitose was the extreme ease of acid hydrolysis of one of the linkages, which had earlier led Alekhine to the discovery of turanose and the trisaccharide nature of melezitose. For years this feature was accepted as virtual proof of the presence of sucrose in the melezitose molecule. However, the opinion that the ease of hydrolysis was evidence for the furanoid form of the D-fructose ring lost all validity with the discovery by Purves and Hudson1 that methyl D-fructopyranoside is hydrolyzed by acids with the same ease as methyl D-fructofuranoside moreover, the ease of hydrolysis never was evidence concerning the a- or /3-configuration of the D-fructose unit in melezitose. ... 

Haynes, L. J., and Nbwth, F. H., The Glycosyl Halides and Their Derivatives, 10, 207-256 Hehrb, Edward J., The Substituted-sucrose Structure of Melezitose, 8, 277-290... 

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