Glucose with sarcosine

Sarcosine (1 g.) and dry, powdered D-glucose (10 g.) in N,N-dimethylformamide (30 ml.) were heated at 100°. Dissolution was complete in ten minutes, and the mixture was heated for a further 30 minutes. The yellow sirup remaining after removal of the solvent under diminished pressure was freed of D-glucose with bakers yeast. After 5 days, paper-chromatographic examination showed that no D-glucose or d-mannose remained. The solution was decolorized and the water was removed by evaporation under diminished pressure. Purification from methanol and ether gave an amorphous powder (2 g., 70% yield), [a]D — 49 1° (in water). 

The complex thioamide lolrestat (8) is an inhibitor of aldose reductase. This enzyme catalyzes the reduction of glucose to sorbitol. The enzyme is not very active, but in diabetic individuals where blood glucose levels can. spike to quite high levels in tissues where insulin is not required for glucose uptake (nerve, kidney, retina and lens) sorbitol is formed by the action of aldose reductase and contributes to diabetic complications very prominent among which are eye problems (diabetic retinopathy). Tolrestat is intended for oral administration to prevent this. One of its syntheses proceeds by conversion of 6-methoxy-5-(trifluoroniethyl)naphthalene-l-carboxyl-ic acid (6) to its acid chloride followed by carboxamide formation (7) with methyl N-methyl sarcosinate. Reaction of amide 7 with phosphorous pentasulfide produces the methyl ester thioamide which, on treatment with KOH, hydrolyzes to tolrestat (8) 2[. 

TVAcylsarcosinates. Sodium IV-lauroylsarcosinate [7631-98-3] is a good soap-like surfactant. Table 4 gives trade names and properties. The amido group in the hydrophobe chain lessens the interaction with hardness ions. N-Acylosarcosinates have been used in dentifrices (qv) where they are claimed to inactivate enzymes that convert glucose to lactic acid in the mouth (57). They are prepared from a fatty acid chloride and sarcosine ... 

Figure 9.18 The oviposition deterrent pheromone of the cherry fruit fly. It consists of a dihydroxystearic acid with a glucose molecule attached as an ether and an amide of the amino-acid sarcosine...

The coreticulation described above [3] is simple to perform during multienzymatic immobilization. The required enzymes are mixed with albumin, and enough glutaraldehyde is added to cross-link the various proteins. This method is also used for the coimmobilization of creatinin amidohydrolase, creatin amidinohydrolase and sarcosine oxidase, to construct a creatinin electrode, and for the coimmobilization of a-glucosidase and glucose oxidase for the determination of starch [40]. 

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