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471844

Sigma-Aldrich

(1R)-(−)-(1-Aminohexyl)phosphonic acid

98%

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About This Item

Empirical Formula (Hill Notation):
C6H16NO3P
CAS Number:
Molecular Weight:
181.17
MDL number:
UNSPSC Code:
12352103

Assay

98%

optical activity

[α]20/D −25°, c = 5 in 1 M NaOH

mp

270-276 °C (lit.)

SMILES string

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

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.

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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
G Lavielle et al.
Journal of medicinal chemistry, 34(7), 1998-2003 (1991-07-01)
A series of new amino phosphonic acid derivatives of vinblastine (1, VLB) has been synthesized and tested in vitro and in vivo for antitumor activity. The compounds were obtained from O4-deacetyl-VLB azide. All of the new products studied were capable
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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