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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:
66254-56-6
Molecular Weight:
153.12
MDL number:
MFCD00797884
UNSPSC Code:
12352116
PubChem Substance ID:
24870765
NACRES:
NA.22

Quality Level

100

assay

98%

optical activity

[α]20/D +1.0°, c = 1 in 1 M NaOH

mp

272-277 °C (lit.)

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

Related Categories

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
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

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)

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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
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
Camp, N.P. et al.
Bioorganic & Medicinal Chemistry Letters, 2, 1047-1047 (1992)
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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