13299-09-7Relevant academic research and scientific papers
Total Synthesis of Pseudomonas aeruginosa 1244 Pilin Glycan via de Novo Synthesis of Pseudaminic Acid
Liu, Han,Zhang, Yanfeng,Wei, Ruohan,Andolina, Gloria,Li, Xuechen
supporting information, p. 13420 - 13428 (2017/10/05)
Pseudaminic acid (Pse) is a nonulosonic acid unique to bacterial species, found as a component of important cell surface glycans and glycoproteins in various pathogenic species, such as the critical hospital threat Pseudomonas aeruginosa. Herein we present the development of a facile and scalable de novo synthesis of Pse and its functionalized derivatives from easily available Cbz-l-allo-threonine methyl ester (16 steps in 11% yield). The key reactions in our de novo synthesis involve the diastereoselective glycine thioester isonitrile-based aldol-type reaction to create the 1,3-anti-diamino skeleton, followed by the Fukuyama reduction and the indium-mediated Barbier-type allylation. Moreover, we have studied the glycosylation of the Pse glycosyl donors and identified the structural determinants for its glycosylation diastereoselectivity, which enabled us to complete the total synthesis of P. aeruginosa 1244 pilin trisaccharide α-5NβOHC47NFmPse-(2→4)-β-Xyl-(1→3)-FucNAc.
The application of aryl substituted derivatives of xylose as environmentally friendly multipurpose pesticides
Belakhov,Garabadzhiu
, p. 3002 - 3007 (2017/07/07)
A series of aryl substituted derivatives of xylose have been synthesized. Biological tests have revealed high fungicidal activity of the resulting compounds against various phythopathogenic fungi. Additional biological studies have demonstrated high plant growth regulatory activity of the compounds synthesized.
Synthetic approach toward the partial sequences of betaglycan in the linkage region on solid support and in solution phase
Tamura, Jun-Ichi,Yamaguchi, Akihiro,Tanaka, Junko,Nishimura, Yuko
, p. 61 - 82 (2008/02/09)
We have synthesized, for the first time, the partial sequence of the betaglycan composed of the tetraosyl hexapeptide, which was directly usable as a probe for enzymatic glycosyl transfer. Stepwise elongation afforded the corresponding tetraosyl trichloro
Synthesis of betaglycan-type tetraosyl hexapeptide: a possible precursor regulating enzymatic elongation toward heparin.
Tamura, Jun-ichi,Yamaguchi, Akihiro,Tanaka, Junko
, p. 1901 - 1903 (2007/10/03)
TETRAOSYL HEXAPEPTIDE, A PART OF THE SEQUENCE OF BETAGLYCAN: beta-D-GlcA-(1-->3)-beta-D-Gal-(1-->3)-beta-D-Gal-(1-->4)-beta-D-Xyl-(1-->O-SerGlyTrpProAspGly (1), which was designed as a probe for glycan elongation toward heparin, was synthesized in a stere
Synthesis of uronic acid-containing xylans found in wood and pulp
Oscarson,Svahnberg
, p. 873 - 879 (2007/10/03)
Two uronic acid-containing trisaccharides, (4-deoxy-β-L-threo-hex-4-enopyranosyluronic acid)- and (4-O-methyl-α-D-gluropyranosyluronic acid)-(1→2)-β-D-xylopyranosyl-(1→4)-D-xylopyranose, found in enzyme hydrolysates from pulp are synthesised. A common dixyloside 2′-OH acceptor, p-methoxyphenyl[3,4-O-(2′,3′-dimethoxybutane-2′,3′- diyl)-β-D-xylopyranosyl]-(1→4)-2,3-di-O-benzoyl-β- D-xylopyranoside, is constructed and coupled with two glucuronate thioglycoside donors differently substituted in the 4-position, O-methyl and O-mesyl, respectively, to give trisaccharides. DMTST as promoter in diethyl ether gives exclusively the α-linked products in high yield. Treatment of the 4″-O-mesyl trisaccharide with DBU then gives the α,β-unsaturated uronic acid derivative. The protection pattern introduced in the acceptor allows continued synthesis of larger oligosaccharides. Removal of the butanedione acetal produces 3′,4′-acceptors, and the p-methoxyphenyl glycoside can be transformed into various glycosyl donors, e.g. thioglycosides and sugar halides. Complete deprotection gives the two target reducing trisaccharides.
Enzymatic β-galactosidation of modified monosaccharides: Study of the enzyme selectivity for the acceptor and its application to the synthesis of disaccharides
Lopez,Fernandez-Mayoralas
, p. 737 - 745 (2007/10/02)
The selectivity of the E. coli β-galactosidase-catalyzed glycosylation of monosaccharides differently substituted at the anomeric position has been studied. Substituents bearing a phenyl ring increase the enzyme-acceptor binding; however, partial enzyme inhibition occurs. The regioselectivity of the glycosylation was dependent on small variations in the monosaccharide acceptor, such as the atom linked to the anomeric carbon and the number of methylenes between this atom and aromatic ring. A schematic model is proposed that accounts for the results. The information from this study allows the direct synthesis of disaccharides, with high regioselectivity and yields ranging from 30 to 40%.
β-D-GLUCOSIDASE-CATALYSED TRANSFER OF THE GLYCOSYL GROUP FROM ARYL β-D-GLUCO- AND β-D-XYLO-PYRANOSIDES TO PHENOLS
Aerts, Guido M.,Opstal, Omer Van,Bruyne, Clement K. De
, p. 221 - 234 (2007/10/02)
The effect of phenols on the hydrolysis of substituted phenyl β-D-gluco- and β-D-xylo-pyranosides by β-D-glucosidase from Stachybotrys atra has been investigated.Depending on the glycon part of the substrate and on the phenol substituent, the hydrolysis is either inhibited or activated.With aryl β-D-glucopyranosides, such transfer does not occur when phenols are used as acceptors, but it does occur with anilines.A two-steps mechanism, in which the first step is partially reversible, is proposed to explain these observations.A qualitative analysis of the various factors determing the overall effect of the phenol is given.
