05260
L-Alanyl-L-1-aminoethylphosphonic acid
≥95% (HPLC)
Synonym(s):
(S)-Alanyl-(R)-1-aminoethylphosphonic acid, Alafosfalin, Alaphosphin
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About This Item
Empirical Formula (Hill Notation):
C5H13N2O4P
CAS Number:
Molecular Weight:
196.14
UNSPSC Code:
51102829
NACRES:
NA.85
PubChem Substance ID:
EC Number:
262-362-8
Beilstein/REAXYS Number:
4801790
MDL number:
InChI
1S/C5H13N2O4P/c1-3(6)5(8)7-4(2)12(9,10)11/h3-4H,6H2,1-2H3,(H,7,8)(H2,9,10,11)/t3-,4+/m0/s1
InChI key
BHAYDBSYOBONRV-IUYQGCFVSA-N
SMILES string
C[C@H](N)C(=O)N[C@@H](C)P(O)(O)=O
assay
≥95% (HPLC)
form
powder
optical activity
[α]20/D −45±2°, c = 1% in H2O
color
white
antibiotic activity spectrum
Gram-negative bacteria, Gram-positive bacteria
mode of action
cell wall synthesis | interferes, enzyme | inhibits
storage temp.
2-8°C
General description
Chemical structure: amino acid derivatives
Application
Alaphosphin is used as a selection agent for isolation of Salmonella and as a dipeptide mimetic antibacterial agent.
Biochem/physiol Actions
Alaphosphin is an antibacterial phosphonopeptide which mimics the terminal dipeptide moiety (D-Ala-D-Ala) of bacterial cell wall peptidoglycan . It metabolizes aminophosphonic acid which inhibits alanine racemase and uridine 5-diphosphate-N-acetylmuramoylalanine synthetase.
Alaphosphin is used as a selection agent for isolation of Salmonella and as a dipeptide mimetic antibacterial agent. It metabolizes aminophosphonic acid which inhibits alanine racemase and uridine 5-diphosphate-N-acetylmuramoylalanine synthetase.
Packaging
250MG
Other Notes
Keep container tightly closed in a dry and well-ventilated place. Store under inert gas. Moisture sensitive. Keep in a dry place.
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Effect of food on the bioavailability of alafosfalin, a new antibacterial agent.
P G Welling et al.
The Journal of antimicrobial chemotherapy, 6(3), 373-379 (1980-05-01)
P Angehrn et al.
Antimicrobial agents and chemotherapy, 25(5), 607-611 (1984-05-01)
The phosphonopeptide L- norvalyl -L-1- aminoethylphosphonic acid [ Nva -Ala(P)] has been studied in combination with 12 beta-lactam antibiotics for activity against Pseudomonas aeruginosa. Nocardicin A was found to give the most potent synergistic combination with Nva -Ala(P). This interaction
M Arisawa et al.
Antimicrobial agents and chemotherapy, 21(5), 706-710 (1982-05-01)
Potentiating activity of alafosfalin was examined in detail with 8 cephalosporins and mecillinam against 164 urinary bacteria representing 8 genera. Alafosfalin was generally comparable in activity to cefamandole and mecillinam but superior to other cephalosporins tested. When the minimal fractional
F R Atherton et al.
Antimicrobial agents and chemotherapy, 15(5), 696-705 (1979-05-01)
The novel antibacterial peptide mimetic alaphosphin (l-alanyl-l-1-aminoethylphosphonic acid) selectively inhibited peptidoglycan biosynthesis in both gram-negative and gram-positive bacteria. It induced accumulation of uridine diphosphate-N-acetyl-muramyl-tripeptide in gram-positive organisms and significantly reduced the intracellular pool levels of d-alanine. Alaphosphin was actively transported
K J Towner et al.
Bulletin of the World Health Organization, 58(5), 747-751 (1980-01-01)
Isolates of Vibrio cholerae obtained immediately after the outbreak of the fourth recorded epidemic of cholera in the United Republic of Tanzania were sensitive to tetracycline, but after five months of its extensive therapeutic and prophylactic use, 76% of the
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