Found 3 publications.
Displayed publications from 1 to 3
Expand all publications
Collapse all publications
Show all as text (SweetDB notation)
Show all graphically (SNFG notation)
1. (Article ID: 1125)
Ragousis V, Leondiadis L, Livaniou E, Evangelatos GP
A simple approach to the synthesis of muramic acid and isomuramic acid: 1H and 13C NMR characterisation
Carbohydrate Research 297(3) (1997)
289-295
A simple and efficient synthesis of 2-amino-3-O-[(R)-1-carboxyethyl]-2-deoxy-D-glucose (muramic acid, 6) and its stereoisomer 2-amino-3-O-[(S)-1-carboxyethyl]-2-deoxy-D-glucose (isomuramic acid, 7) from methyl 2-acetamido-4,6-O-benzylidene-2-deoxy-a-D-glucopyranoside (1) is described. Condensation of the O-3 oxyanion of 1 with an excess of methyl (R,S)-2-bromopropionate, followed by alkaline hydrolysis of the crude product and subsequent acidification, afforded crystalline methyl 2-acetamido-4,6-O-benzylidene-3-O-[(R,S)-1-carboxyethyl]-2-deoxy-a-D-glucopyranoside (2), in 72% yeld, as a mixture of diastereomers. Esterification of 2 with an excess of diazomethane afforded quantitatively the corresponding mixture of epimeric esters, which were very easily separated by column chromatography on silica gel, giving pure (R) and (S) epimeric esters. Removal of the benzylidene and acetyl groups by acid hydrolysis gave, respectively, muramic acid (6), in 95% yield and isomuramic acid (7), in 93% yield. 1H and 13C NMR data are given.
NMR, synthesis, acid, 13C NMR, characterisation, 1H NMR, approach, isomuramic acid, muramic acid, 2-acetamido-2-deoxyglucosides
Publication DOI: 10.1016/S0008-6215(96)00271-6Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Department of Chemistry, Laboratory of Organic Chemistry, University of Athens, Panepistimiopolis, Zographou, 15771 Athens, Greece, Immunochemistry Laboratory, Institute of Radioisotopes and Radiodiagnostic Products, National Centre for Scientific Research ''Demokritos'', Ag. Paraskeui, 153 IOAthens, Greece
Methods: 13C NMR, 1H NMR
The publication contains the following compound(s):
Expand this publication
Collapse this publication
2. (Article ID: 2327)
Schweda E
Structural studies of some bacterial lipopolysaccharides and NMR and conformational studies of some mono- and disaccharide derivatives
Chemical Communications 3 (1987)
1-42
Journal NLM ID: 9610838Publisher: Cambridge: Royal Society of Chemistry
The publication contains the following compound(s):
- Compound ID: 5505
|
a-Colp-(1-6)-+
|
a-Colp-(1-3)-a-D-Glcp-(1-4)-a-D-Galp-(1-3)-b-D-GlcpNAc |
Show graphically |
Structure type: oligomer
Compound class: LPS
Reference(s) to other database(s): GTC:G36088XJ, GlycomeDB:
6993
- Compound ID: 5506
|
a-Colp-(1-3)-b-D-Galp-(1-3)-b-D-GlcpNAc-(1-3)-a-D-Galp-(1-3)-b-D-GalpNAc |
Show graphically |
Structure type: oligomer
Compound class: LPS
Reference(s) to other database(s): GTC:G91235RS, GlycomeDB:
6994
- Compound ID: 3844
Structure type: polymer chemical repeating unit
Trivial name: O-unit
Compound class: O-polysaccharide, LPS
Reference(s) to other database(s): GlycomeDB:
33731
Expand this publication
Collapse this publication
3. (Article ID: 2328)
Minami Y, Yazawa K, Tamura Z, Tanaka T, Yamamoto T
Selectivity of utilization of galactosyl-oligosaccharides by bifidobacteria
Chemical and Pharmaceutical Bulletin 31 (1983)
1688-1691
Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
The publication contains the following compound(s):
- Compound ID: 5507
Structure type: oligomer
Trivial name: lactosylfructoside
Reference(s) to other database(s): GTC:G32232EA, GlycomeDB:
7087, CCSD:
22517, CBank-STR:6453
Expand this publication
Collapse this publication
Total list of publication IDs on all result pages of the current query:
Total list of corresponding CSDB IDs (permanent record IDs):
Execution: 2 sec