Skip to Content
Merck
All Photos(1)

Documents

05260

Sigma-Aldrich

L-Alanyl-L-1-aminoethylphosphonic acid

≥95% (HPLC)

Synonym(s):

(S)-Alanyl-(R)-1-aminoethylphosphonic acid, Alafosfalin, Alaphosphin

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C5H13N2O4P
CAS Number:
60668-24-8
Molecular Weight:
196.14
Beilstein:
4801790
EC Number:
262-362-8
MDL number:
MFCD01569244
UNSPSC Code:
51102829
PubChem Substance ID:
329747669
NACRES:
NA.85

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

SMILES string

C[C@H](N)C(=O)N[C@@H](C)P(O)(O)=O

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

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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
Recent developments in the field of phosphonic acid antibiotics.
M Neuman
The Journal of antimicrobial chemotherapy, 14(4), 309-311 (1984-10-01)
Decreased intravenous glucose tolerance and low plasma insulin response in spiny mice. (Acomys cahirinus).
A Gutzeit et al.
Diabetologia, 10 Suppl, 667-670 (1974-11-01)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service