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367559

Sigma-Aldrich

(S)-(+)-1-Aminoethylphosphonic acid

99%

Synonym(s):

D-(+)-1-Aminoethylphosphonic acid, D-Ala(P)

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About This Item

Linear Formula:
CH3CH(NH2)P(O)(OH)2
CAS Number:
66068-76-6
Molecular Weight:
125.06
Beilstein:
4291033
MDL number:
MFCD00066503
UNSPSC Code:
12352116
PubChem Substance ID:
24862769
NACRES:
NA.22

Quality Level

100

Assay

99%

form

solid

optical activity

[α]20/D +4.8°, c = 5 in H2O

mp

290 °C (dec.) (lit.)

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-/m0/s1

InChI key

UIQSKEDQPSEGAU-REOHCLBHSA-N

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Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

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

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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V Copié et al.
Biochemistry, 27(14), 4966-4970 (1988-07-12)
Inhibition of alanine racemase from the Gram-positive bacterium Bacillus stearothermophilus by (1-aminoethyl) phosphonic acid (Ala-P) proceeds via a two-step reaction pathway in which reactivation occurs very slowly. In order to determine the mechanism of inhibition, we have recorded low-temperature, solid-state
O Ploux et al.
European journal of biochemistry, 259(1-2), 63-70 (1999-01-23)
8-Amino-7-oxopelargonate synthase catalyzes the first committed step of biotin biosynthesis in micro-organisms and plants. Because inhibitors of this pathway might lead to antibacterials or herbicides, we have undertaken an inhibition study on 8-amino-7-oxopelargonate synthase using six different compounds. d-Alanine, the
D A Mironenko et al.
Biokhimiia (Moscow, Russia), 55(6), 1124-1131 (1990-06-01)
Penicillin acylase from E. coli (EC 3.5.1.11) was found to hydrolyze N-phenylacetylated 1-aminoethylphosphonic acid and its esters. The enzyme preferentially converts the R-form of the substrates: the ratios of the bimolecular rate constants of penicillin acylasecatalyzed hydrolysis of R- and
F R Atherton et al.
Journal of medicinal chemistry, 29(1), 29-40 (1986-01-01)
Phosphonodipeptides and phosphonooligopeptides based on L- and D-(1-aminoethyl)phosphonic acids L-Ala(P) and D-Ala(P) and (aminomethyl)phosphonic acid Gly(P) at the acid terminus have been synthesized and investigated as antibacterial agents, which owe their activity to the inhibition of bacterial cell-wall biosynthesis. A

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