Sugars 1-acetamido derivatives

Mycosamine differs from most of the other amino sugars isolated from antibiotic substances in not being V-methylated.86 The tetraacetate XXVI of mycosamine (XXV) can be isolated by acetolysis of nystatin or of the antifungal antibiotic substance amphotericin B, and it yields the acetamido derivative XXVII on catalytic deacetylation. 

Attempts to obtain 4-acetamido sugars from derivatives of 6-deoxy-D- or L-mannose led to the discovery of an interesting rearrangement that is suitable for the preparation of 5-acetamido-5,6-dideoxy-D- or... 

Syntheses of amino-alditol derivatives are covered in Chapters 18 and 19, and the introduction of a 2-acetamido-function into a sugar formazan derivative is covered in Chapter 10. 

Class Amino sugar" (usually as acetamido (W-acetyl) derivative Uronic acid Uronate Ulosonic acid Ulosonate The sialic acid family ... 

Amide derivatives have proved especially useful sugars for study by c.d. spectroscopy. The amide substituent is the same as the chromophore found in proteins, so that its optical properties have been extensively studied both experimentally and theoretically. 2-Acetamido sugars are found in many glycoproteins. The structure of 2-acetamido-2-deoxy-a-D-glucopyranose is given as an example in formula 7. 

Listowsky and coworkers showed that the c.d. of this sugar derivative is due entirely to lactic acid, and confirmed that this chromophore is in the D configuration for muramic acid. N-Acetylmuramic acid, in which the amino group is replaced by an amido group at C-2, has a c.d. spectrum that is roughly a linear combination of the lactic acid in muramic acid and the amide in 2-acetamido-2-deoxy-D-glucose. This indicates that the amide chromophore and the lactic acid chromophore in N-acetylmuramic acid behave independently. 

S. Hanessian and T. H. Haskell, Synthesis of 5-acetamido-5-deoxypentoses. Sugar derivatives containing nitrogen in the ring, J. Org. Chem., 28 (1963) 2604-2610. 

In a paper concerned primarily with the determination of neutral sugars, Richey and coworkers examined the O-trimethylsilyl derivatives of 2-acetamido-2-deoxy-D-glucose and 2-acetamido-2-deoxy-D-galactose.171 Similar methods for determining these compounds have also been used in studies on human milk,545 yeasts and bacteria,1,2 blood-group oligosaccharides,405 and urine.118 These methods were also included in a model study on the isothermal determination of sugars.256... 

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