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471860

Sigma-Aldrich

(1R)-(+)-(1-Amino-2-methylpropyl)phosphonic acid

98%

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About This Item

Linear Formula:
(CH3)2CHCH(NH2)P(O)(OH)2
CAS Number:
Molecular Weight:
153.12
MDL number:
UNSPSC Code:
12352116
PubChem Substance ID:
NACRES:
NA.22

Assay

98%

optical activity

[α]20/D +1.0°, c = 1 in 1 M NaOH

mp

272-277 °C (lit.)

functional group

amine

SMILES string

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

InChI

1S/C4H12NO3P/c1-3(2)4(5)9(6,7)8/h3-4H,5H2,1-2H3,(H2,6,7,8)/t4-/m1/s1

InChI key

DGSLPJDIFKVSIB-SCSAIBSYSA-N

General description

The enantiodiscrimination of (1R)-(+)-(1-amino-2-methylpropyl)phosphonic acid from its enantiomer in the gas-phase can be done using ESI-MS-CID technique. [electrospray ionization-mass spectrometric detection-collision induced dissociation]

Application

Serves as an attractive substitute for amino carboxylic acids in biological systems. Exhibits interesting and useful properties as peptide analog, antiviral agent, hapten for the generation of catalytic antibodies, enzyme inhibitors, potent antibiotics, herbicides, and pesticides.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard 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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Enantiodiscrimination of chiral a-aminophosphonic acids by mass spectrometry.
Paladini A, et al.
Chirality, 13(10), 707-711 (2001)
Nour Z Atwany et al.
Biology, 9(8) (2020-08-13)
Regulatory T cells (Tregs) are key players in the regulation of inflammatory responses. In this study, two natural molecules, namely, sparteine sulfate (SS) and harpagoside (Harp), were investigated for their ability to induce Tregs in human peripheral blood mononuclear cells
Camp, N.P. et al.
Bioorganic & Medicinal Chemistry Letters, 2, 1047-1047 (1992)
M C Allen et al.
Journal of medicinal chemistry, 32(7), 1652-1661 (1989-07-01)
The synthesis of five amino phosphorus derivatives, 1a-e, is described. The derivatives were incorporated into a series (18) of analogues of the 5-14 portion of angiotensinogen, in most cases at the scissile Leu-Val bond. The resultant compounds were tested in
J Bird et al.
Journal of medicinal chemistry, 37(1), 158-169 (1994-01-07)
The synthesis of a series of N-phosphonalkyl dipeptides 6 is described. Syntheses were devised that allowed the preparation of single diastereoisomers and the assignment of stereochemistry. The compounds were evaluated in vitro for their ability to inhibit the degradation of

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