Mannitol and Erythritol

Figure 2.8. Formation of mannitol and erythritol. Adapted from Veiga-da-Cunha et at. (1993) with the kind permission of the Journal of Bacteriology.

Among the existing polyols, namely mannitol, sorbitol, erythritol, galactitol, xylitol, ribitol, lactitol and maltitol (Figure 18.1), only mannitol and erythritol are naturally produced by LAB (Vrancken et al. 2010). 

Separated polyols are detected by a variety of reagents, including ammoniacal silver nitrate (175), concentrated sulfuric acid, potassium permanganate (163), lead tetraacetate, and potassium teUuratocuprate (176). A mixture of sodium metaperiodate and potassium permanganate can be used to detect as htde as 5—8 ).tg of mannitol or erythritol (177). 

Initially, attempts to grow the organism on sodium acetate as the sole source of carbon were unsuccessful, but the difficulties were overcome and mannitol, arabinitol, erythritol, glycerol, maltose, and a,a-trehalose were produced. This was a useful development because conditions were established for the incorporation of [14C] acetate, thereby making labeled polyols and disaccharides available. 

Figure 17-17. Arabitol, dulcitol, erythritol, glycerol, inositol, mannitol, and sorbitol.

Alkyl tethered alcohols such as D-mannitol and L-erythritol [20], have been used to bring cinnamyl units together for photocycloadditions. However, this probably involves cycloaddition between an excited enone moiety and the tethered alkene. Other examples of carbon linked alkenes include perhaps the earliest example of alkene+alkene photocycloaddition. Liu and Hammond [21] reported the formation of cyclobutane from the triplet irradiation of myrcene (see Sch. 11). 

Alditols - made by reducing the carbonyl group of a sugar. The resulting polyhydroxy compounds are called alditols. Important ones include erythritol, D-mannitol, and D-glucitol (also called sorbitol). 

Like mannitol and sorbitol, erythritol (see here also) is an alditol - a molecule created by reducing the carbonyl group of the corresponding sugar (in this case, erythrose). 

It has also been shown that lipase CA can produce reduced sugar-containing polyesters regioselectively from divinyl sebacate and sorbitol, in which sorbitol was exclusively acylated at the 1 and 6-positions (Scheme 23.11) [115]. Mannitol and meso-erythritol were also regioselectively polymerized with divinyl sebacate. The lipase CA-catalyzed polycondensation of adipic acid and sorbitol also took place in... 

Table 1 shows the separation of alcohols (2,3-butanediol, ethanol, methanol), glycols (glycerol), alditols (erythritol, arabitol, sorbitol, galactitol, mannitol), and carbohydrates (rhamnose, arabinose, glucose, galactose, lactose, sucrose, raffinose, maltose) using a CarboPac MAI column set with 480 mM sodium hydroxide eluent... 

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