Darstellung von 2-azido-2-desoxy-d-glucopyranose und z, 4-diazido-2,4-didesoxy-d-glucopyranose

Paulsen, Hans; Koebernick, Hubert; Stenzel, Wolfgang; Köll, Peter

doi:10.1016/s0040-4039(00)72177-0

Cited by 25 publications

(9 citation statements)

References 5 publications

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“…In our hands attempts at direct aminolysis of 7 using methanolic ammonia, or using sodium azide and ammonium chloride (in DMF at 140 °C) both failed, however, success with these reactions have been reported by others. 49 An alternative approach to 8 using reaction of iodide 6 with excess teteramethylguanidium azide in DMF (120 °C, 3 days) is known from the literature. 25 The structure of azide 8 was confirmed by X-ray crystallography.…”

Section: Resultsmentioning

confidence: 99%

Total Synthesis of N-Acetylglucosamine-1,6-anhydro-N-acetylmuramylpentapeptide and Evaluation of Its Turnover by AmpD from Escherichia coli

et al. 2009

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The bacterial cell wall is recycled extensively during the course of cell growth. The first recycling event involves the catalytic action of the lytic transglycosylase enzymes, which produce an uncommon 1,6-anhydropyranose 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-d-muramylpeptide, 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-d-glucosamine-(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-d-glucosamine-(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, an enzyme that removes the peptide from the disaccharide scaffold in the early cytoplasmic phase of cell wall turnover.

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Section: Resultsmentioning

confidence: 99%

Total Synthesis of N-Acetylglucosamine-1,6-anhydro-N-acetylmuramylpentapeptide and Evaluation of Its Turnover by AmpD from Escherichia coli

et al. 2009

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“…1 ) and its derivatives (e.g., 2 and 3 ) are of great interest due to their integral role in bacterial cell wall recycling [ 1 – 2 ] and the induction of antibacterial resistance [ 3 ]. Numerous syntheses of 1 have been carried out, including early synthetic work by Sinaÿ [ 4 – 5 ] and Paulsen [ 6 – 7 ], and more recent syntheses by Mobashery [ 8 ], Fukase [ 9 ], and Mark [ 10 ], which have enabled further studies in the field of antibacterial research.…”

Section: Introductionmentioning

confidence: 99%

An efficient synthesis of 1,6-anhydro-N-acetylmuramic acid from N-acetylglucosamine

Calvert¹,

Mayer²,

Titz³

2017

Beilstein J. Org. Chem.

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“…Levoglucosan, however, readily allows a combination of the functionalisation at C(4) and the substitution of HOÀC(2) by an azido group [15]. We decided to use the anhydrogalactose 7 as starting material.…”

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“…Epoxide-ring opening with NaN 3 and NH 4 Cl in boiling EtOH/H 2 O [15] [17] gave the gluco-azide 11 (73%). This was reduced to the amine 12 (71 ± 77%) with LiAlH 4 in THF or Mg/I 2 in MeOH.…”

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Oligosaccharide Analogues of Polysaccharides Part 25

Stichler-Bonaparte

Bernet

Vasella

2002

HCA

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F¸r Oskar Jeger mit herzlichen Gl¸ckw¸nschen zum 85. GeburtstagThe ethynylated gluco-azide 11 was prepared from the dianhydrogalactose 7 by ethynylation, transformation into the dianhydromannose 10, and opening of the oxirane ring by azide (Scheme 1). The retentive alkynylating ring opening of 11 and of the corresponding amine 12 failed. (2-Acetamidoglucopyranosyl)acetylenes were, therefore, prepared from the corresponding mannopyranosylacetylenes. Retentive alkynylating ring opening of the partially protected b-d-mannopyranose 15, possessing a C(3)ÀOH group, gave a 85 : 15 mixture of 16 and the (E)-enyne 17. The alkyne 16 was deprotected to the tetrol 18 that was selectively protected and transformed into the C(2)ÀO triflate 20. Treatment with NaN 3 in DMF afforded a 85 : 15 mixture of the b-dgluco configured azide 21 and the elimination product 22. Similarly, the a-d-mannopyranosylacetylene 23 was transformed into the azide 26. Retentive alkynylating ring opening of the ethynylated anhydromannose 28 gave the expected b-d-mannopyranosyl 1,4-dialkyne 29 as the main product besides the diol 28, the triol 31, and the (E)-enyne 30 (Scheme 2). This enyne was also obtained from 31 by a stereoselective carboalumination promoted by the cis (axial) HOÀC(2) group. Deprotection of the dialkynylated mannoside 31 led to 32, whereas selective silylation, triflation, and azidation gave a 3 : 7 mixture of the 1-ethynylglucal 35 and the b-d-gluco azide 36, which was transformed into the diethynylated b-d-GlcNAc analogue 38. Similarly, the diethynylated a-dmannopyranoside 39 was transformed into the disilylated a-d-GlcNAc analogue 41, and further into the diol 42 and the monosilyl ether 43 (Scheme 5). Eglinton coupling of 41 gave the symmetric buta-1,3-diyne 44, which did not undergo any further Eglinton coupling, even under forcing conditions. However, Eglinton coupling of the monosilyl ether 43 and subsequent desilylation gave the C 1 -symmetric cyclotrimer 45 in moderate yields.

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Darstellung von 2-azido-2-desoxy-d-glucopyranose und z, 4-diazido-2,4-didesoxy-d-glucopyranose

Cited by 25 publications

References 5 publications

Total Synthesis of N-Acetylglucosamine-1,6-anhydro-N-acetylmuramylpentapeptide and Evaluation of Its Turnover by AmpD from Escherichia coli

Total Synthesis of N-Acetylglucosamine-1,6-anhydro-N-acetylmuramylpentapeptide and Evaluation of Its Turnover by AmpD from Escherichia coli

An efficient synthesis of 1,6-anhydro-N-acetylmuramic acid from N-acetylglucosamine

Oligosaccharide Analogues of Polysaccharides Part 25

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