Carbohydrates by Marcel Florkin; Elmer H Stotz

By Marcel Florkin; Elmer H Stotz

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Can be used not only to establish the ring size of glycosides but also the configuration of the glycosidic link. IX-o-Hexopyranosides reduce two moles of periodic acid, release a mole of formic acid and all yield the same diglycollic dialdehyde derivative (CXI). This has lost the asymmetric centres at C-2. CHpH (,{,- ;-:-0"" o~ C~OH \J ~o ;Yo Methyl a-D-Glucoside 1. Sr, ¥) J10CH 2. ) 0 "0 \ tHCOOH ;10CH / s,,-o c) ~0 (CXII) (CXI) C-3 and C-4, while those at C-I and C-5 are unchanged. In the case of P-Dhexopyranosides the configuration on C-I is reversed in the dialdehyde.

P_h_. ~4~1~ OAe (CLXXVI) (CLXXVII) The esters of toluene p-sulphonic acid (tosyl) and methane sulphonic acid (mesyl)88 of special interest because their removal can yield anhydrosugars (p. 52), are prepared in the usual way by the action of the acid chloride in anhydrous pyridine solution. Hydrogenolysis with lithium aluminium hydride of the tosyl and mesyl groups from secondary hydroxyl groups can result in two different types of fission (a) and (b) with the formation respectively of the parent sugar and a new deoxy-sugar 89 .

Whereas the constitution of p-glucosan (CCXV) I~ "OC~ OH "19 CH:! (CCXVII) (CCXVIII) 9 55 AMINO-SUGARS was established by reaction with periodate, the two furanose I,6-anhydrides (CCXVII, CCXVIII), in spite of the presence of adjacent hydroxyl groups on C-2 and C-3, are immune to attack by this reagent. 9. Amino-sugars The common naturally occurring amino-sugars are glucosamine (z-aminoz-deoxy-n-glucose) (CCXIX) and galactosamine (z-amino-z-deoxy-n-galactose) (CCXXI) 100a. In addition there are a few unusual examples synthesised by the Actinomyces species of moulds, talosamine found in cartilage and a curious C-linked mannosamine (CCXX) present in neuraminic acid.

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