Sophorolipids

Sophorolipid is a glycolipid, ie it is composed of carbohydrate and lipid. It therefore contains moieties of widely different oxidation levels and its synthesis from single demand carbon sources has a high ATP demand. However, the demand for ATP is reduced if a mixture of glucose and C-18 alkane is used. If glucose and fatty add is used the ATP demand is reduced further and relatively high spedfic production rates can be achieved. 

Is a low or a high growth efficiency for the produdng organism desirable for sophorolipid production Explain your reasoning. 

A high growth effidency (high YoT)is desirable because sophorolipid production has a high demand for ATP. 

Scheme 89 Total synthesis of sophorolipid lactone 449 by sequential RCAM and -selective partial hydrogenation [186]...

Sophorolipid lactone (34) was obtained from an open-chain bisalkyne precursor (concomitant formation of 2-butyne) in a macrocyclization yield of 78% [29], The epothilones have been obtained through non-stereoselective alkene metathesis [26d], making them worthwhile targets for the combination alkyne metathesis/Lindlar hydrogenation to assemble the C12-C13 Z double bond. Furthermore, epothilone C (35) shows the most complex array of functional groups among the substrates of alkyne metathesis. The macrocyclization yield, starting from the expected OTBS-protected precursor (not shown) was 81% [23, 30]. Neither... 

Sophorolipids (SLs) are extracellular glycolipids that are normally synthesized from glucose and a fatty acid source (either FFA or triacylglycerol) by a number of yeasts (primarily Candida bombicola). They are composed of a disaccharide (sophorose 2-O-P-D-glucopyranosyl-p-D glucopyranose) attached to a hydroxy fatty acyl moiety at the co-1 or co carbon (Fig. 7.5). Typi-... 

Figure 7.5. Sophorolipid (17-L-(. 2 -0-P-glucopyranosyl-P-D-glucopyranosyl]-oxy)-9-cis-octadecenoic acid T,4"-lactone 6, 6"-diacetate (A) and its free-acid form (B).

TABLE 7.3. Fermentation of glycerol (pure vs. crude) to sophorolipids by C. bombicola and the effect on predominant structural form. 

Carr, J. A., and Bisht, K. S. 2003. Enzyme-catalyzed regioselective transesterilication of peracetylated sophorolipids. Tetrahedron Lett., 59, 7713-7724. 

Nunez, A., Ashby, R. D., Foglia, T. A., and Solaiman, D. K. Y. 2001. Analysis and characterization of sophorolipids by liquid chromatography with atmospheric pressure chemical ionization. Chromatographia, 53, 673-677. 

Furstner, A., Radkowski, K., Grabowski, J., Wirtz, C., Mynott, R. Ring-Closing Alkyne Metathesis. Application to the Total Synthesis of Sophorolipid Lactone. J. Org. Chem. 2000, 65, 8758-8762. 

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