Centre National De La Recherche Scientifique

Université´ D'aix-Marseille

Université Paris-Saclay

Jordi Mas Pons

Boris Vauzeilles

Sam Dukan

Aurélie Baron

Aurelie Baron

Aurèlie Baron

Laura Fourmois

The invention relates to a method for labeling specifically living bacteria, comprising the steps of: a) incubating said bacteria of said sample with at least one modified monosaccharide compound comprising a first reactive chemical group capable to chemically react with a second reactive group, so that a residue bearing said first reactive group is incorporated into the envelope of such bacteria, and b) contacting said modified monosaccharide residue incorporated within the envelope of the bacteria with a labeling molecule comprising a said second reactive group, for generating the chemical reaction of said first reactive group with said second reactive group, characterized in that said modified monosaccharide compound has the following formula (I), or a salt thereof: Wherein &#x2014;A, B and C can be independently H, OH, NH, OH and NHbeing substituted or not by protecting groups thereof and &#x2014;D is an alkyl chain in Cto C, each carbon being substituted or not by OH or NH, OH and NHbeing substituted or not by protecting groups thereof and &#x2014;at least one of A, B, C or D groups is substituted by a said first reactive group. 

Method for labeling specifically living bacteria comprising the use of modified non endogenous monosaccharide compounds

The invention relates to a method for labeling specifically living microorganisms in a sample comprising microorganisms, the method comprising the steps of: a) incubating said microorganisms of said sample with at least one modified monosaccharide compound comprising a first reactive chemical group capable to chemically react with a second reactive group, so that a residue bearing said first reactive group is incorporated into such microorganisms, and b) contacting said residue incorporated in the microorganisms, with a labeling molecule comprising a said second reactive group, for generating the chemical reaction of said first reactive group of said residue incorporated within said living microorganisms with said second reactive group of said labeling molecule, resulting in a covalent link, characterized in that the said modified monosaccharide compound has the following formula (I'), or a salt thereof: &#x2014;X can be O, NH or S, preferably O and NH, and &#x2014;R1 and R2 can be independently H, OH, NH, OH and NHbeing substituted or not by protecting groups thereof, preferably substituted by alkyl, hydroxyalkyl, acyl, formyl or imidoyl groups, and &#x2014;R3 is H or an alkyl chain in Cto C, each carbon being substituted or not substituted by OH or NHsubstituted or not by protecting groups thereof, preferably by alkyl, hydroxyalkyl, acyl, formyl or imidoyl groups, and &#x2014;at least one of X, R1, R2 and R3 groups, preferably R3, being substituted by a said first reactive group Ra. 

Method for labeling specifically living microorganisms comprising the use of modified monosaccharide compounds

Disclosed are new compounds of formulae: Wherein: Rand Rcan be independently H; a Cto Calkyl including methyl, ethyl, propyl, butyl; aryl including phenyl, para-methoxyphenyl; or R,Rtogether with the carbon C-6 can be a cyclopentylidene or cyclohexylidene; each of these groups being substituted or not; and Rcan be a Cto Calkyl including methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl; or aryl including phenyl, methylphenyl, ethylphenyl, each of these groups being substituted or not. The invention also relates to their method of manufacture and their use for the synthesis of Ara-N, Kdo-Nand 4eKdo-N.

5-azido-5-deoxy-2 :3-isopropylidene-D-arabinose compounds; their method of manufacture and their use for the synthesis of ARA-N3, KDO-N3 and 4EKDO-N3

Disclosed is a method of preparation of 6-azido-2,4-diacetamido-2,4,6-trideoxy--mannose. This method includes the chemical reaction of compound of formula X: Wherein: Rcan be a Cto Calkyl including methyl, ethyl, isopropyl; aryl including phenyl; each of these groups being substituted or not; and Rcan be a Cto Calkyl including methyl, ethyl, isopropyl, tert-butyl, isobutyl; each of these groups being substituted or not; with a deprotecting reagent including a Lewis or Br&#xf6;nsted acid in a polar aprotic solvent, thereby obtaining a free C-1 OH group. The method can also start with the preparation from commercially available-galactose pentaacetate,-galactose tetraacetate or tetraacetyl-galactosyl trichloroacetimidate. The step of deprotecting the anomeric position avoids the use of cerium and allows the easy purification of 6-azido-2,4-diacetamido-2,4,6-trideoxy--mannose.

Method of preparation of 6-azido-2,4-diacetamido-2,4,6-trideoxy-D-mannose

The invention relates to a method for labeling specifically living bacteria of a given category of Gram negative bacteria in a sample comprising bacteria, the method including the steps of:

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Jordi Mas Pons