2- amino-2-deoxy occurrence

Folic acid, 4-amino-4-deoxy-10-methyl-, 1, 164 3, 325 as anticancer drug, 1, 263 biological activity, 3, 325 Folic acid, 4-amino-10-methyl-toxicity, 1, 141 Folic acid, 7,8-dihydro-biosynthesis, 3, 320 synthesis, 1, 161, 3, 307 Folic acid, 4-dimethylamino-hydrolysis, 3, 294 Folic acid, 5-formiminotetrahydro-biological activity, 3, 325 Folic acid, 5-formyl-5,6,7,8-tetrahydro-biological activity, 3, 325 chirality, 3, 281 occurrence, 3, 325 Folic acid, 10-forfnyltetrahydro-biological activity, 3, 325 Folic acid, 5,10-methenyl-5,6,7,8-tetrahydro-biological activity, 3, 325 chirality, 3, 281 Folic acid, 5-methyl-chirality, 3, 281 Folic acid, 9-methyl-toxicity, 1, 141... 

Isolated chitins are highly ordered copolymers of 2-acetamido-2-deoxy-/3-D-glucose and 2-amino-2-deoxy-j6-D-glucose. The occurrence of the latter is explained by the fact that in vivo chitin is covalently finked to proteins via the nitrogen atom of approximately one repeating unit out of ten, therefore upon isolation a degree of deacetylation close to 0.10 is found. Chito-biose, 0-(2-amino-2-deoxy-j6-D-glucopyranosyl)-(l 4)-2-amino-2-deoxy-... 

The oxidation of the a-amino acids has not been completely studied, but it appears to be slow in most cases.8-9 The organic sulfide linkage is oxidized by periodate to a sulfone, with the concomitant liberation of iodine,48 but the oxidation of a 1-deoxy-l-thioglycoside, without occurrence of this side reaction, has been carried out at least once (in very dilute solution).44... 

N. catarrhalis,560 N. perflava,559 Moraxella duplex and Micrococcus calco-aceticus,443 and Escherichia coli,420 Vicari and Kabat,45 in studies of blood-group oligosaccharides, and Hellerqvist and colleagues,53 in an examination of the common core-polysaccharide of Salmonella typhimurium, have used similar methods. The examination of amino sugars as their peracetylated aminodeoxyalditols has also been used by Liideritz and colleagues72 to establish the occurrence of 4-amino-4-deoxy-L-arabinose in Salmonella lipopolysaccharides, and has been extended to aminodeoxyheptoses by Williams and Perry.561... 

AraNAc 4-acetamido-Ara 4-ace tamido-Xyl 3% ECNSS-M 190 occurrence in Salmonella of 4-amino-4-deoxy-L-arabinose 72... 

The occurrence of some substitution in the deamination of 2-amino-2-deoxy-/3-D-mannopyranosides131 152 (72), and its absence in the reaction of the a-D-pyranoside150 69, must be due to the steric effect of the axial anomeric substituent which (in the a-D-pyran-oside) hinders the approach of the nucleophile (water) to either the C-2 carbonium ion or to C-2 of the diazonium ion. The glucose and glucitol tentatively detected as minor products in the deamination of 72 (R = D-glucose residue and R = D-glucitol residue) presumably arose by way of a hydride shift of H-l to C-2. 2-Deoxy-D-glucono-1,5-lactone (75) was not detected, as it would probably have. o,... 

When hydride shifts occur in the deamination of axial amines, cleavage of ether or glycosidic functions may result. The small amount of glucose tentatively identified151 in the product of deamination of 6-0-(2-amino-2-deoxy-/3-D-mannopyranosyl)-D-glucose (72 see p. 47) can be attributed to the occurrence of a hydride shift of H-l to C-2. 

In O Scheme 1, O Scheme 2 and O Scheme 3, some of the important representatives of natural monosaccharides are presented and compiled by the three different classes deoxy-sugars, amino-sugars, and branched-chain sugars. O Table 1 lists their names and natural sources of occurrence. 

There has been substantial activity in the synthesis of 3-amino-2,3,6-trideoxy-hexoses and their di-A-methyl derivatives as a result of their wide occurrence in antibiotics. In a paper of substantial proportions, Bartner et alP have synthesized by standard reactions all four possible methyl 2,3,6-dideoxy-3-dimethylamino-a-D-hexopyranosides (and some /3-anomers) as well as the corresponding L-ribo isomer (L-megosaminide). Syntheses have been reported for D-ristosamine (3-amino-2,3,6-trideoxy-D-rz7 o-hexose) from methyl 2-deoxy-D-amfcmo-hexo-pyranoside and of the isomeric 3-amino-2,3,6-trideoxy-L-Jcy/o-hexose (1) from methyl 2,6-dideoxy-L- mZ>mo-hexopyranoside, using standard sequences involving azidej displacement of sulphonate esters for introducing the nitrogen. 

The occurrence of 2-amino-2-deoxy-D-gIucosyl residues in the cell-wall peptidoglycan of group A Streptococcus pyogenes type 4 has been confirmed. ... 

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