60687-36-7

Basic information

• Product Name: (R)-(-)-1-AMINOETHYL-PHOSPHONIC ACID
• Synonyms: (R)-(-)-1-PHOSPHONOETHYLAMINE;(R)-(-)-1-AMINOETHYL-PHOSPHONIC ACID;(R)-1-AMINO-ETHYLPHOSPHONIC ACID;(1R)-1-PHOSPHONO-1-ETHANAMINE;D-1-AMINO-ETHYLPHOSPHONIC ACID;H-R-ALA(P)-OH;H-D-AETPO-(OH)2;H-D-ALAP-(OH)2
• CAS NO: 60687-36-7
• Molecular Formula: C₂H₈NO₃P
• Molecular Weight: 125.06
• Mol File: 60687-36-7.mol
• Article Data: 5

Chemical Properties

• Melting Point: 290 °C (dec.)(lit.)
• Boiling Point: 319.2 °C at 760 mmHg
• Flash Point: 146.9 °C
• Appearance: /
• Density: 1.475 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• CAS DataBase Reference: (R)-(-)-1-AMINOETHYL-PHOSPHONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-1-AMINOETHYL-PHOSPHONIC ACID(60687-36-7)
• EPA Substance Registry System: (R)-(-)-1-AMINOETHYL-PHOSPHONIC ACID(60687-36-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: 3261
• WGK Germany: 3
• Hazardous Substances Data: 60687-36-7(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 60687-36-7 differently. You can refer to the following data:
1. Di- to tetrapeptides with this amino acid analogue at the "P-terminal" are bactericides and synergistic potentiators of penicillins and cephalophorins
2. (R)-(?)-1-Aminoethylphosphonic acid can be used to prepare copper(II) heteroligand complexes, which are employed in the solution equilibrium studies.

Definition

ChEBI: An optically active phosphonic acid having a 1-aminoethyl group attached to the phosphorus.

General Description

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

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

Upstream product

• 79879-28-0 (D)-1-(N-phenylacetylamino)ethylphosphonic acid 
• 65576-94-5 (-)-1-aminoethylphosphonous acid 
• 81069-92-3 (L,D)-1-(N-phenylacetylamino)ethylphosphonic acid 
• 6323-97-3 1-aminoethanephosphonic acid 
• 126306-95-4 Diphenyl-N-(benzyloxycarbonyl)-L-leucyl-(2-decarboxy-L-alanin-2-yl)phosphonat 

Downstream Products

• 60668-54-4 (1R)-1-[(N-benzyloxycarbonyl-L-phenylalanyl)amino]-ethylphosphonic acid 
• 98820-75-8 [(R)-1-((R)-2-Benzyloxycarbonylamino-propionylamino)-ethyl]-phosphonic acid 
• 60668-26-0 1-R-1-[(N-benzyloxycarbonyl-L-alanyl)amino]ethanephosphonic acid 
• 60687-34-5 (R)-<1-(N-carbobenzoxyamino)ethyl>phosphonic acid 
• 6881-54-5 (1-oxoethyl)phosphonic acid 
• 60668-55-5 L-Phe-L-Ala(P) 
• 71447-87-5 phosphonic acid 
• 60668-24-8 (1R)-1-(L-alanylamino)-ethylphosphonic acid 
• 137037-32-2 tris(trimethylsilyl) 1-aminoethylphosphonate 

Relevant articles and documents

Biocatalytic resolution of enantiomeric mixtures of 1-aminoethanephosphonic acid

Several fungal strains, namely Bauveria bassiana, Cuninghamella echinulata, Aspergillus fumigatus, Penicillium crustosum and Cladosporium herbarum, were used as biocatalysts to resolve racemic mixtures of 1-aminoethanephosphonic acid using L/D amino acid oxidase activity. The course of reaction was analyzed by 31P-NMR in the presence of cyclodextrin used as chiral discriminating agent. The best result (42% e.e of R-isomer) was obtained with a strain of Cuninghamella echinulata.

Preparation of optically active 1-aminoalkylphosphonic acids by stereoselective enzymatic hydrolysis of racemic N-acylated 1-aminoalkylphosphonic acids

N-Phenylacetylated derivatives of 1-aminoalkylphosphonic acids were synthesized and high enantioselectivity of their hydrolysis by penicillin acylase (EC 3.5.1.11) was demonstrated. Stereoselective enzymatic hydrolysis of racemic 1-(N-phenylacetylamino) alkylphosphonic acids was used for preparation of enantiomeric 1-aminoalkylphosphonic acids. The kinetic regularities of penicillin acylase catalyzed hydrolysis were established and the biocatalytic process was optimized to increase the optical purity and the yield of the optically active product.

1-Aminoalkylphosphonous Acids. Part 1. Isosteres of the Protein Amino Acids

The synthesis of 1-aminoalkylphosphonous acids, isosteres of the protein amino acids, by addition of hypophosphorous acid to diphenylmethylimines is described.These analogues of glycine, alanine, valine, leucine, isoleucine, phenylalanine, tyrosine, tryptophan, serine, threonine, methionine, cysteine, cystine, glutamic acid, lysine, ornithine, arginine, and proline have been prepared and the analogues of alanine, valine, leucine, phenylalanine, and methionine resolved.The alanine, valine and methionine analogues have interesting antimicrobial activity and the alanine analogue has plant growth inhibiting properties.Oxidation of the appropriate 1-aminoalkylphosphonous acids gave the 1-aminoalkylphosphonic acid analogues of (+/-)-alanine, (-)-alanine, (+/-)-valine, (-)-valine, (+/-)-serine, (+/-)-threonine, (+/-)-lysine, (-)-leucine, and (+/-)-ornithine.