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05260

Sigma-Aldrich

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:
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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

05260-VAR:
05260-BULK:
05260-250MG:
05260-1G:

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’.

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W H Traub
Chemotherapy, 26(2), 103-110 (1980-01-01)
Alaphosphin (Ro 03--7008; S-alanyl-R-1-aminoethyl-phosphonic acid) proved active against most of 53 strains of Serratia marcescens tested. The majority of strains were inhibited by less than or equal to 64 micrograms/ml of the drug; concentrations of greater than or equal to
R P Tomkiewicz et al.
The European respiratory journal, 7(1), 81-87 (1994-01-01)
N-acetylcysteine L-lysinate Nacystelyn (L-NAC) is a newly synthesized mucolytic agent, of which the action in vivo has not been well defined. In six healthy mongrel dogs, the rheological properties of mucus, its mucociliary and cough clearability, and the transepithelial potential
F R Atherton et al.
Antimicrobial agents and chemotherapy, 18(6), 897-905 (1980-12-01)
Dipeptide variants of alafosfalin (L-alanyl-L-1-aminoethylphosphonic acid) with substantial differences in potency and antibacterial spectrum in vitro and in vivo have been synthesized. Certain dipeptides with alternatives to the L-alanyl residue had broader antibacterial spectra; activity against Pseudomonas aeruginosa was included.
C Henning et al.
Chemotherapy, 28(3), 185-188 (1982-01-01)
The pharmacokinetics of alafosfalin and ampicillin were studied in rabbits. Serum concentrations were compared to levels in subcutaneous tissue fluid obtained from implanted tissue cages. The concentrations of alafosfalin exceeded those of ampicillin and the drugs were eliminated at similar
Alafosfalin, a new synthetic antibacterial compound.
F E Hahn
Die Naturwissenschaften, 68(2), 90-90 (1981-02-01)
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