Glucopyranosyl amides

A number of amide- and ester-linked fatty acids and (/ )-3-hydroxy acids are components of the lipid A part in the LPS from Gram-negative bacteria. The acids have been tabulatedand the chemistry of lipid A summarized. The most common acids in lipid A from Enterobacteriaceae are the saturated 12 0,14 0, and 16 0, and the (/ )-3-hydroxy-14 0, The last is linked to N-2 and 0-3 of the 2-amino-2-deoxy-D-glucopyranosyl residues, and the others are ester-linked to the hydroxy acid, as in the lipid A (44) of Salmonella minnesota. Other linear and branched fatty acids, unsaturated acids, S)-2- and (/ )-3-hydroxy acids, and 3-oxotetradecanoic acid are components of lipid A from certain different species. In the lipid A from Rhizobium trifolii, 2,7-dihydroxyoctanoic acid is linked as amide to a 2-amino-2-deoxy-D-gl ucopy ranosy 1 residue. ... 

Simultaneously with the studies just described, acylated nitriles of aldobionic acids were also investigated, and several hexosyl-pentose amides were isolated. Ammonolysis of octa-O-acetylcellobiononitrile (59) afforded55 l,l-bis(acetamido)-l-deoxy-3-0-/3-D-glucopyranosyl-D-arabinitol (60), N-acetyl-3-0-/3-D-glucopyranosyl-D-arabinofuranos-ylamine (61), and a 3-0-/3-D-glucopyranosyl-D-arabinose not previously described in the literature. 

Heparosine. A sulfated disaccharide has been isolated308 by partial, acidic hydrolysis of heparin, and it has been formulated as 4-0-(2-amino-2-deoxy-a-v-glucopyranosyl 6-sulfate)-D-glucuronic acid. Heparosine and its W-acetyl amide are amorphous. An amorphous disaccharide prepared by a similar procedure, was, however, believed309 to be a 2-amino-2-deoxy-(D-glucosyluronic acid)-D-glucose. 

Llewellyn DB, Arndtsen BA (2005) Synthesis of a library of chiral a-amino acid-based borate counteranions and their application to copper catalyzed olefin cyclopropanation. Tetrahedron Asymmetry 16 1789-1799 Makino T, Baba N, Oda J, Inouye Y (1977) Asymmetric reduction of alpha, beta-unsaturated iminuum salt with A-glucopyranosyl-l,4-dihydronicotin-amides. Chemlnd 1977 277-278... 

Teira-0-acetyl-P- p-glucopyranosyl isoihkicyanaie (GITC) l-Eluoro-2,4-dinitrophcnyl-5-L-alaninc amide (Marfey s rcagem)... 

The carbene-generating biotinylated 2-acetamido-2-deoxy-D-glucopyranosyl-amide diazirine derivative 54 and the lactoside 55 have been synthesized for photoaffinity labelling of P-(l ->4)-galactosyl transferase and GMj synthase. ... 

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