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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 [1][2]. 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

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Certificates of Analysis (COA)

Lot/Batch Number
0000188741
127M4817V
077M4771V
066M4776V
BCBM2268V

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Alafosfalin, a new synthetic antibacterial compound.
F E Hahn
Die Naturwissenschaften, 68(2), 90-90 (1981-02-01)
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
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
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.
A Caretta et al.
European journal of biochemistry, 153(1), 49-53 (1985-11-15)
The high-affinity binding of the cGMP analogue 8-(5-thioacetamidofluorescein)-cGMP to rod outer segment membranes depleted of peripherally bound proteins has been defined by equilibrium dialysis (mean +/- SD): membranes contain about one cGMP binding site per 130 rhodopsin molecules; the concentration
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