Deoxy-D-glucose

Deoxy-D-glucose 5,6-O-Isopropyli-den-l-(nitro-methyl)- E2le, 4851 (OH CH2-N02)... 

In extending this direct method of synthesis, we next investigated the possibility of preparing similarly constituted halides from 2-deoxy-D-arabino-hexose (2-deoxy-D-glucose) (21). The hexose was subjected to a partial anomerization procedure described by Bergmann and co-workers (1). The solid material obtained by this procedure is a mixture of the anomeric forms of 2-deoxy-D-arabino-hexose low temperature p-nitro-benzoylation of the latter in pyridine resulted in a mixture of crystalline, anomeric tetrakis-p-nitrobenzoates in a ratio of approximately 1 1. They were readily separable by fractional recrystallization, and treatment of either with an excess of hydrogen bromide in dichloromethane, or with... 

Figure 1. Oxidation of 2-deoxy-D-glucose (6 10 4M) with sodium metaperiodate (6.6 10 SM) in 0.1N H2SO4 (curve A) and in unbuffered solution (curve...

Rennie (49), working in my laboratory, succeeded in converting d-glucose into 4-deoxy-D-Jct/Zo-hexose, albeit with considerable difficulty, by the following sequence of reactions which incorporate mercaptalation of the carbonyl group and reductive desulfurization of the dithiol 1 2 D-glucose methyl 2,3-di-0-benzyl-6-0-trityl-a-D-glucopyranoside - ... 

Acetamido-2-deoxy-D-glucose, reaction with acetyl chloride, 46,1... 

Amino 2 deoxy d glucose, conversion of hydrochloride to 2 acetamido-2 deoxy d glucose, 46, 2 l-(Ammomcthyl) cycloheptanol, 46, 31 2 Amino 2 methyl 1 propanol in isolation of levopimanc acid 45, 64 c-Amino p nitrobiphenyl, by nitration of o aminobiphenyl, 46, 86 from o,p dimtrobiphenyl, 46, 88 Amino 2 propanone, semicarbazone... 

Muramic acid (Mur) 2-Amino-3- 0-[(fl)-1 -carboxyethyl]-2-deoxy-D-glucose... 

Nigerose Nojirimycin Noviose a-D-Glucopyranosyl-(1- 3)-D-glucose 5- Amino-5-deoxy-D-glucopyranose 6- Deoxy-5-C-methyl-4-Omethyl-L-/yxo-hexose... 

The first known 1-carboxyethyl ether of a sugar was 2-amino-3-0-[(/ )-l-carboxyethyl]-2-deoxy-D-glucose or muramic acid (37). It is a component of the polysaccharide moiety of the peptidoglycan in the bacterial cell-wall. It is partially replaced by the mamo isomer, 2-amino-3-6>-[(/ )-l-carboxy-ethyl]-2-deoxy-D-mannose, in the peptidoglycan from Micrococcus lyso-deikticus. 

The a anomers of 2-acetamido-2-deoxy-D-glucose and 2-acetamido-2-deoxy-D-galactose have the same nir c.d. bands in 1 1 methanol-water at 0° as the anomeric mixtures have in aqueous solution. This indicates that the anomeric configuration has little influence on the nir c.d. band. 

Heparin HEP L-iduronic acid 2-amino-2-deoxy-D-glucose a-IdoA-2S-(l—4)-a-GlcNS-6S-(l —4)- (1—4)-0-(a-L-idopyranosyluronic acid 2-sulfate)-(l—4)-(2-deoxy-2-sulfamino-a-D-glucopyranosyl 6-sulfate)-... 

D-Clucuronic acid residues in heparin are linked as in disaccharide units 1 and 2, that is, either to 2-acetamido-2-deoxy-D-glucose ( Ana) or to 2-deoxy-2-sulfoamino (ANS) residues. (Although not apparent from Scheme 1, the amino sugar can be sulfated at C-6.)... 

Residues of non-N-substituted 2-amino-2-deoxy-D-glucose constitute only a tiny fraction (if any) of the total amino sugar of heparin and heparan sulfate. Although free amino groups are produced in the biosynthesis20,23 of heparin (between stages 1 and 2, see Scheme 1), the small proportions occasionally found in heparin and heparan sulfate preparations are most probably the result of some N-desulfation during extraction, or purification, or both. 

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