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06655

Sigma-Aldrich

(R)-(−)-1-Aminoethylphosphonic acid

≥97.0% (NT)

Synonym(s):

L-(−)-1-Aminoethylphosphonic acid, L-Ala(P)

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About This Item

Linear Formula:
CH3CH(NH2)P(O)(OH)2
CAS Number:
Molecular Weight:
125.06
Beilstein:
4291032
MDL number:
UNSPSC Code:
12352116
PubChem Substance ID:
NACRES:
NA.22

Assay

≥97.0% (NT)

optical activity

[α]20/D −4.8±0.5°, c = 5% in H2O

storage temp.

2-8°C

SMILES string

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

InChI

1S/C2H8NO3P/c1-2(3)7(4,5)6/h2H,3H2,1H3,(H2,4,5,6)/t2-/m1/s1

InChI key

UIQSKEDQPSEGAU-UWTATZPHSA-N

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General description

(R)-(-)-1-Aminoethylphosphonic acid is a synthetic analog of L-alanine that shows antibacterial property.

Application

(R)-(−)-1-Aminoethylphosphonic acid can be used to prepare copper(II) heteroligand complexes, which are employed in the solution equilibrium studies.

Other Notes

Di- to tetrapeptides with this amino acid analogue at the "P-terminal" are bactericides and synergistic potentiators of penicillins and cephalophorins.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

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

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Reaction of Alanine Racemase with 1-Aminoethylphosphonic Acid Forms a Stable External Aldimine
Stamper CGF, et al.
Biochemistry, 37(29), 10438-10445 (1998)
F R Atherton et al.
Antimicrobial agents and chemotherapy, 15(5), 677-683 (1979-05-01)
Peptide mimetics with C-terminal residues simulating natural amino acids have been designed as inhibitors of bacterial cell wall biosynthesis. The phosphonopeptide series consisting of various l and d residues of natural amino acids combined with 1-aminoalkyl (and aryl-alkyl-) phosphonic acid
J G Allen et al.
Antimicrobial agents and chemotherapy, 16(3), 306-313 (1979-09-01)
The metabolism and pharmacokinetics of a synthetic antibacterial phosphonodipeptide, alafosfalin, have been studied in rats, baboons, and human volunteers. The compound was rapidly absorbed from the injection site after subcutaneous and intramuscular administration and gave peak plasma concentrations at 15
Stabilities and coordination modes of α-alaninephosphonic acid in copper (II) heteroligand complexes with ethylenediamine, diethylenetriamine or N, N, N′, N′, N″-pentamethyldiethylene triamine in aqueous solution
Kamecka A, et al.
Journal of Solution Chemistry, 40(6), 1041-1054 (2011)
Phosphonopeptides, a new class of synthetic antibacterial agents.
J G Allen et al.
Nature, 272(5648), 56-58 (1978-03-02)

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