Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C3H7NO2 |
| Molecular Weight | 89.0932 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@@H](N)C(O)=O
InChI
InChIKey=QNAYBMKLOCPYGJ-UWTATZPHSA-N
InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m1/s1
| Molecular Formula | C3H7NO2 |
| Molecular Weight | 89.0932 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
D-alanine is an isomer of non-essential L-amino acid. D isomer is found in the cell walls of bacteria, but not in bacterial proteins. It was discovered, that being an endogenous agonist of the glycine site of the N-methyl-d-aspartate (NMDA) receptor, D-alanine can have beneficial effects on schizophrenia.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Resistance to D-cycloserine in the tubercle bacilli: mutation rate and transport of alanine in parental cells and drug-resistant mutants. | 1971 May |
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| The genome of Mycobacterium leprae: a minimal mycobacterial gene set. | 2001 |
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| Sequencing of the ddl gene and modeling of the mutated D-alanine:D-alanine ligase in glycopeptide-dependent strains of Enterococcus faecium. | 2001 Apr |
|
| Interplant alkaloid variation and Senecio vernalis toxicity in cattle. | 2001 Jun |
|
| Rapid identification of Enterococcus durans and Enterococcus hirae by PCR with primers targeted to the ddl genes. | 2001 Oct |
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| Antecedent treatment with different antibiotic agents as a risk factor for vancomycin-resistant Enterococcus. | 2002 Aug |
|
| First characterization of a cluster of VanA-type glycopeptide-resistant Enterococcus faecium, Colombia. | 2002 Sep |
|
| Lateral gene transfer and ancient paralogy of operons containing redundant copies of tryptophan-pathway genes in Xylella species and in heterocystous cyanobacteria. | 2003 |
|
| Using bifunctional polymers presenting vancomycin and fluorescein groups to direct anti-fluorescein antibodies to self-assembled monolayers presenting d-alanine-d-alanine groups. | 2003 Apr 16 |
|
| A six amino acid deletion, partially overlapping the VanSB G2 ATP-binding motif, leads to constitutive glycopeptide resistance in VanB-type Enterococcus faecium. | 2003 Nov |
|
| Nosocomial infection with vancomycin-dependent enterococci. | 2004 Jul |
|
| Phylogenomics of the reproductive parasite Wolbachia pipientis wMel: a streamlined genome overrun by mobile genetic elements. | 2004 Mar |
|
| Identification of a G protein-coupled receptor specifically responsive to beta-alanine. | 2004 May 28 |
|
| Cephalosporin-resistant pneumococci and sickle cell disease. | 2005 Aug |
|
| D-Amino acid dipeptide production utilizing D-alanine-D-alanine ligases with novel substrate specificity. | 2005 Jun |
|
| Conformational and quantitative characterization of oritavancin-peptidoglycan complexes in whole cells of Staphylococcus aureus by in vivo 13C and 15N labeling. | 2006 Apr 7 |
|
| Substrate specificity of thermostable D-alanine-D-alanine ligase from Thermotoga maritima ATCC 43589. | 2006 Nov |
|
| [Chemical constituents from leaves of Morus multicaulis]. | 2007 Apr |
|
| Diazenedicarboxamides as inhibitors of D-alanine-D-alanine ligase (Ddl). | 2007 Apr 1 |
|
| Structure of cymbidine A, a monomeric peptidoglycan-related compound with hypotensive and diuretic activities, isolated from a higher plant, Cymbidium goeringii (Orchidaceae). | 2007 May |
|
| Characterization of new L,D-endopeptidase gene product CwlK (previous YcdD) that hydrolyzes peptidoglycan in Bacillus subtilis. | 2007 Oct |
|
| X-ray structures of two proteins belonging to Pfam DUF178 revealed unexpected structural similarity to the DUF191 Pfam family. | 2007 Oct 1 |
|
| An expanded set of amino acid analogs for the ribosomal translation of unnatural peptides. | 2007 Oct 3 |
|
| Crystallization and preliminary crystallographic analysis of D-alanine-D-alanine ligase from Streptococcus mutans. | 2007 Sep 1 |
|
| Expression, crystallization and preliminary X-ray crystallographic analysis of Xoo0352, D-alanine-D-alanine ligase A, from Xanthomonas oryzae pv. oryzae. | 2008 Dec 1 |
|
| Discovery of new inhibitors of D-alanine:D-alanine ligase by structure-based virtual screening. | 2008 Dec 11 |
|
| A review of telavancin in the treatment of complicated skin and skin structure infections (cSSSI). | 2008 Feb |
|
| D-Alanine:D-alanine ligase as a new target for the flavonoids quercetin and apigenin. | 2008 Nov |
|
| Enzymatic characterization and crystal structure analysis of the D-alanine-D-alanine ligase from Helicobacter pylori. | 2008 Sep |
|
| Staphylococcus epidermidis: a differential trait of the fecal microbiota of breast-fed infants. | 2008 Sep 10 |
|
| Novel type of Streptococcus pneumoniae causing multidrug-resistant acute otitis media in children. | 2009 Apr |
|
| ATP competitive inhibitors of D-alanine-D-alanine ligase based on protein kinase inhibitor scaffolds. | 2009 Feb 1 |
|
| Comparative genomic analyses of nickel, cobalt and vitamin B12 utilization. | 2009 Feb 10 |
|
| Mutation in a D-alanine-D-alanine ligase of Azospirillum brasilense Cd results in an overproduction of exopolysaccharides and a decreased tolerance to saline stress. | 2009 Jan |
|
| Enterococcal surface protein Esp is not essential for cell adhesion and intestinal colonization of Enterococcus faecium in mice. | 2009 Jan 29 |
|
| Structure of D-alanine-D-alanine ligase from Thermus thermophilus HB8: cumulative conformational change and enzyme-ligand interactions. | 2009 Oct |
|
| Genome subtraction for novel target definition in Salmonella typhi. | 2009 Oct 11 |
|
| Molecular characterization of glycopeptide-resistant enterococci from hospitals of the picardy region (france). | 2010 |
|
| Crystal structure of the Apo form of D-Alanine:D-Alanine ligase (DDl) from Streptococcus mutans. | 2010 Aug |
|
| Selenocysteine, pyrrolysine, and the unique energy metabolism of methanogenic archaea. | 2010 Aug 17 |
|
| Aza-1,2,3-triazole-3-alanine synthesis via copper-catalyzed 1,3-dipolar cycloaddition on aza-progargylglycine. | 2010 Aug 6 |
|
| Molecular orientation and intermolecular interaction in alanine on Cu(001). | 2010 Feb 16 |
|
| Role of Arg301 in substrate orientation and catalysis in subsite 2 of D-alanine:D-alanine (D-lactate) ligase from Leuconostoc mesenteroides: a molecular docking study. | 2010 Jun |
|
| Proteomic characterization of vanA-containing Enterococcus recovered from Seagulls at the Berlengas Natural Reserve, W Portugal. | 2010 Sep 21 |
Sample Use Guides
It was studied the effect of D-alanine (10 mM), D-leucine (10 mM), D-methionine (10 mM), D-tryptophan (10 mM), and D-tyrosine (10 uM and 1 mM) on biofilm formation in two commonly studied laboratory strains of P. aeruginosa: PAO1 and PA14. In strains PAO1 and PA14, the addition of D-amino acids did not result in an inhibitory effect on biofilm growth in 24-well plates. Repeating the study in 96-well plates confirmed the findings that D-amino acids do not inhibit biofilm formation of P. aeruginosa. It was concluded that D-amino acids only slow the production of biofilms rather than completely prevent biofilm formation.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 02:17:38 UTC 2023
by
admin
on
Sat Dec 16 02:17:38 UTC 2023
|
| Record UNII |
E3UDS4613U
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
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DTXSID3045649
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