13089-18-4Relevant articles and documents
A mechanistic study on the α-N-acetylgalactosaminidase from E. meningosepticum: A family 109 glycoside hydrolase
Chakladar, Saswati,Shamsi Kazem Abadi, Saeideh,Bennet, Andrew J.
, p. 1188 - 1192 (2014/08/05)
A recombinant glycoside hydrolase family 109 α-N- acetylgalactosaminidase from the pathogenic bacteria E. meningosepticum catalyses the hydrolysis of aryl 2-acetamido-2-deoxy-α-d- galactopyranosides. The sensitivities to leaving group abilities (βlg values) on V and V/K are -0.08 ± 0.06 and -0.31 ± 0.12, respectively. These results are consistent with an E2 elimination following hydride transfer from C3. This journal is the Partner Organisations 2014.
Facile synthesis of nitrophenyl 2-acetamido-2-deoxy-α-D- mannopyranosides from ManNAc-oxazoline
Krenek, Karel,Simon, Petr,Weignerova, Lenka,Fliedrova, Barbora,Kuzma, Marek,Kren, Vladimir
, p. 428 - 432 (2012/05/05)
The synthetic procedures for a large-scale preparation of o- and p-nitrophenyl 2-acetamido-2-deoxy-α-D-mannopyranoside are described. The synthetic pathway employs the glycosylation of phenol with ManNAc oxazoline, followed by nitration of the aromatic moiety yielding a separable mixture of the o- and p-nitrophenyl derivative in a 2:3 ratio.
Synthesis of sulfated phenyl 2-acetamido-2-deoxy-D-galactopyranosides. 4-O-Sulfated phenyl 2-acetamido-2-deoxy-β-D-galactopyranoside is a competitive acceptor that decreases sulfation of chondroitin sulfate by N-acetylgalactosamine 4-sulfate 6-O-sulfotransferase
Sawada, Toshihiko,Fujii, Sonoko,Nakano, Hirofumi,Ohtake, Shiori,Kimata, Koji,Habuchi, Osami
, p. 1983 - 1996 (2007/10/03)
We have previously cloned N-acetylgalactosamine 4-sulfate 6-O-sulfotransferase (GalNAc4S-6ST), which transfers sulfate from 3′-phosphoadenosine 5′-phosphosulfate (PAPS) to the C-6 hydroxyl group of the GalNAc 4-sulfate residue of chondroitin sulfate A and forms chondroitin sulfate E containing GlcA-GalNAc(4,6-SO4) repeating units. To investigate the function of chondroitin sulfate E, the development of specific inhibitors of GalNAc4S-6ST is important. Because GalNAc4S-6ST requires a sulfate group attached to the C-4 hydroxyl group of the GalNAc residue as the acceptor, the sulfated GalNAc residue is expected to interact with GalNAc4S-6ST and affect its activity. In this study, we synthesized phenyl α- or -β-2-acetamido-2-deoxy-β-D-galactopyranosides containing a sulfate group at the C-3, C-4, or C-6 hydroxyl groups and examined their inhibitory activity against recombinant GalNAc4S-6ST. We found that phenyl β-GalNAc(4SO4) inhibits GalNAc4S-6ST competitively and also serves as an acceptor. The sulfated product derived from phenyl β-GalNAc(4SO4) was identical to phenyl β-GalNAc(4,6-SO 4). These observations indicate that derivatives of β-D-GalNAc(4SO4) are possible specific inhibitors of GalNAc4S-6ST.
Conjugate addition of phenols to 2-nitrogalactal - Synthesis of O-(2-acetamido-2-deoxygalactosyl) tyrosine
Khodair, Ahmed I.,Winterfeld, Gottfried A.,Schmidt, Richard R.
, p. 1847 - 1852 (2007/10/03)
2-Nitrogalactal derivative 1 afforded 2-deoxy-2-nitrogalactopyranosides on treatment with phenol and substituted derivatives under base catalysis. Transformation of the nitro group into the amino and the acetamido groups and O-deprotection could readily be performed, thus providing aryl 2-acetamido2-deoxygalactopyranosides 5 and 6 in high yields and with good stereoselectivities. The same reaction sequence could also be successfully applied to N-Boc-protected tyrosine methyl ester, to afford the O-galactopyranonsyl tyrosine derivative 10. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
