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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/REAXYS Number:
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

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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’.

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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
[Antibiotics of the phosphonic acid group].
M S Poliak
Antibiotiki i meditsinskaia biotekhnologiia = Antibiotics and medical biotechnology, 32(1), 66-75 (1987-01-01)
Alafosfalin, a new synthetic antibacterial compound.
F E Hahn
Die Naturwissenschaften, 68(2), 90-90 (1981-02-01)
S F Grappel et al.
Antimicrobial agents and chemotherapy, 27(6), 961-963 (1985-06-01)
Alafosfalin, an antibacterial phosphonodipeptide requiring peptide transport for activity, was tested for activity against clinical strains of anaerobic bacteria in peptide-free Roche Sensitivity Test Medium no. 5 agar. It was active against Bacteroides spp., Fusobacterium nucleatum, and Clostridium perfringens but
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.
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