50447-92-2Relevant academic research and scientific papers
Preparation of diamino pseudodisaccharide derivatives from 1,6-anhydro-β-d-hexopyranoses via aziridine-ring cleavage
Kroutil, Jiri,Budesinsky, Milos
, p. 147 - 153 (2007)
Twelve positional isomers of diamino pseudodisaccharide derivatives with gluco-gluco configuration have been prepared using aziridine-ring cleavage of epimino derivatives of 1,6-anhydro-β-d-hexopyranoses of the d-allo, d-manno, and d-galacto configuration
Total synthesis of n-acetylglucosamine-1,6-anhydro-n- acetylmuramylpentapeptide and evaluation of its turnover by ampd from escherichia coli
Hesek, Dusan,Lee, Mijoon,Zhang, Weilie,Noll, Bruce C.,Mobashery, Shahriar
supporting information; experimental part, p. 5187 - 5193 (2009/09/30)
The bacterial cell wall is recycled extensively during the course of cell growth. The first recycling event involves the catalytic action of thelytic transglycosylase enzymes, which produce an uncommon 1,6-anhydropy ranose moiety during separation of the muramyl residues from the peptidoglycan, the major constituent of the cell wall. This product, an N-acetyl-β-D-glucosamine- (1→4)-1,6-anhydro-N-acetyl-β-Dmuramylpeptide, is either internalized to initiate the recycling process or diffuses into the milieu to cause stimulation of the pro-inflammatory responses by the host. We report the total syntheses of N-acetyl-β-Dglucosamine-( 1→4)-1,6-anhydro-N-acetyl- β-D-muramyl-L-Ala-γ-D-Glu-meso-DAP-D-Ala-D-Ala (compound 1, the product of lytic transglycosylase action on the cell wall of Gram-negative bacteria) and N-acetyl-β-Dglucosamine-( 1→4)-1,6-anhydro-N-acetyl- β-D-muramyl-L-Ala-γ-D-Glu-L-Lys-D-Ala-D-Ala (compound 2, from lytic transglycosylase action on the cell wall of Gram-positive bacteria). The syntheses were accomplished in 15 linear steps. Compound 1 is shown to be a substrate of the AmpD enzyme of the Gram-negative bacterium Escherichia coli, anenzyme that removes the peptide from the disaccharide scaffold in the e arly cytoplasmic phase of cell wall turnover.
Improved Procedure for the Selective N-Debenzylation of Benzylamines by Diisopropyl Azodicarboxylate
Kroutil, Jiri,Trnka, Tomas,Cerny, Miloslav
, p. 446 - 450 (2007/10/03)
The selective deprotection of N-benzyl group was achieved in the presence of azido, O-benzyl, and N-tosyl groups in reactions of benzylamines derived from 1,6-anhydro-β-D-glucopyranose with diisopropyl azodicarboxylate (DIAD) in THF. The key role of this solvent and the reaction pathway are presented together with proven reaction intermediates.
Selective N-debenzylation of benzylamino derivatives of 1,6-anhydro-β-D-hexopyranoses
Kroutil, Jiri,Trnka, Tomas,Cerny, Miloslav
, p. 1681 - 1683 (2007/10/03)
(matrix presented) When the series of 2-, 3-, and 4-(benzylamino)-2-, 3-, and 4-deoxy derivatives of 1,6-anhydro-β-D-hexopyranoses in the D-gluco, D-lyxo, and D-arabino configurations were reacted with diisopropyl azodicarboxylate, N-benzyl groups were selectively cleaved in the presence of O-benzyl groups. The yields ranged from 51 to 97percent. The debenzylation of some aliphatic benzylamines is also discussed.
Preparation of 23-dideoxy-2,3-epimino and 3,4-dideoxy-3,4-epimino derivatives of 1,6-anhydro-β-D-hexopyranoses by Mitsunobu reaction
Kroutil, Jiri,Trnka, Tomas,Budesinsky, Milos,Cerny, Miloslav
, p. 813 - 825 (2007/10/03)
A series of new 2-, 3-and 4-benzylamino-2-, 3-and 4-deoxy derivatives of 1,6-anhydro-β-D-hexopyranoses were prepared from 1,6:2,3-and 1.6:3,4-dianhydro-β-D-hexopyranoses by treatment with benzylamine and converted into 2,3-(N-benzylepimino)-2,3-dideoxy-and 3,4-(N-benzylepimino)-3,4-dideoxy-β-D-hexopyranoses of the D-allo, D-galacto and D-talo configuration by Mitsunobu reaction. The structures of benzylamino and benzylimino derivatives were confirmed by 1H and 13C NMR spectra.
