102735-53-5

Basic information

• Product Name: L-CYCLOPROPYLALANINE
• Synonyms: Cyclopropanepropanoicacid, a-aMino-, (aS)-;L-Cyclopropylanine;H-β-Cyclopropyl-L-Alanine;(S)-2-(cyclopropylamino)propanoic acid;(2S)-2-amino-3-cyclopropylpropanoic acid;H-?-Cyclopropyl-L-Alanine99%;L-Ala(β-cyclopropyl)-OH;(S)-2-AMINO-3-CYCLOPROPYL-PROPIONIC ACID
• CAS NO: 102735-53-5
• Molecular Formula: C₆H₁₁NO₂
• Molecular Weight: 129.16
• Product Categories: Amino Acids;Unusual amino acids;pharmacetical;Amino Acid Derivatives;a-amino
• Mol File: 102735-53-5.mol

Chemical Properties

• Boiling Point: 258 °C at 760 mmHg
• Flash Point: 109.9 °C
• Appearance: white crystalline powder
• Density: 1.218 g/cm³
• Vapor Pressure: 0.00994mmHg at 25°C
• Refractive Index: 1.496
• Storage Temp.: -15°C
• PKA: 2.32±0.10(Predicted)
• CAS DataBase Reference: L-CYCLOPROPYLALANINE(CAS DataBase Reference)
• NIST Chemistry Reference: L-CYCLOPROPYLALANINE(102735-53-5)
• EPA Substance Registry System: L-CYCLOPROPYLALANINE(102735-53-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 102735-53-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
L-CYCLOPROPYLALANINE is used as a key intermediate in the synthesis of optically active pyrrolidineacetic acids. These compounds serve as CCR5 receptor antagonists, which exhibit antiviral activity against HIV. By targeting the CCR5 receptor, these antagonists can inhibit the entry of the virus into host cells, thus playing a crucial role in the development of antiviral therapies.

InChI:InChI=1/C6H11NO2/c1-4(6(8)9)7-5-2-3-5/h4-5,7H,2-3H2,1H3,(H,8,9)/t4-/m0/s1

Upstream product

• 102693-69-6 (S)-2-Benzyloxycarbonylamino-3-cyclopropyl-propionic acid benzyl ester 
• 133992-69-5 N-acetyl-3-cyclopropylalanine 
• 113741-17-6 (S)-2-amino-3-cyclopropylpropionic acid benzyl ester 
• 849340-24-5 2-tert-butoxycarbonylamino-3-cyclopropylacrylic acid benzyl ester 
• 406681-37-6 (2S)-2-tert-butoxycarbonylamino-3-cyclopropyl-propionic acid benzyl ester 
• 200482-55-9 4-cyclopropylmethylene-2-phenyl-4H-oxazol-5-one 
• 1027976-19-7 cyclopropylacetamidomalonic acid 
• 174543-84-1 diethyl cyclopropylacetamidomalonate 
• 1198408-99-9 (1S)-1-methyl-2-oxo-2-tetrahydro-1H-pyrrolylethyl 2-bromo-3-cyclopropylpropanoate 
• 1198409-01-6 (1S)-1-methyl-2-oxo-2-tetrahydro-1H-pyrrolylethyl N-(p-methoxyphenyl)-2-amino-3-cyclopropylpropanoate 

Downstream Products

• 61-90-5 L-leucine 
• 327-57-1 L-Norleucine 
• 300853-97-8 2-(S)-hydroxy-3-(cyclopropyl)propanoic acid 
• 457059-27-7 (S)-3-cyclopropylalanine tert-butyl ester 
• 457059-31-3 (S)-2-[4,4-bis(trifluoromethyl)-3-(4-(3-(2-methylphenyl)ureido)-3-methoxybenzyl)-2,5-dioxoimidazolidin-1-yl]-2-(cyclopropylmethyl)acetic acid 
• 457059-32-4 ethyl (S)-3-((S)-2-(4,4-bis(trifluoromethyl)-3-(4-(3-(2-methylphenyl)ureido)-3-methoxybenzyl)-2,5-dioxoimidazolidin-1-yl)-2-(cyclopropylmethyl)acetylamino)-3-phenylpropionate 
• 686339-90-2 3-cyclopropyl-N-[(2-nitrophenyl)sulfonyl]-L-alanine 
• 89483-06-7 (2S)-2-[[(tert-butoxy)carbonyl]amino]-3-cyclopropylpropanoic acid 
• 732231-41-3 methyl (S)-2-amino-3-cyclopropylpropanoate 
• 1038393-52-0 (S)-2-amino-3-cyclopropylpropan-1-ol 
• 177913-96-1 (S)-3-Cyclopropyl-2-[((2S,6R)-2,6-dimethyl-piperidine-1-carbonyl)-amino]-propionic acid benzyl ester 
• 206438-31-5 methyl (S)-2-amino-3-cyclopropylpropanoate hydrochloride 

Relevant articles and documents

Phosphinoferrocenylaminophosphines as novel and practical ligands for asymmetric catalysis

(Matrix Presented) A new series of ligands with a novel phosphine-aminophosphine ligation design as depicted in structure 1 has been prepared on a ferrocenylethyl backbone. These BoPhoz ligands of structure 2 have afforded exceedingly high activity and enantioselectivity in the rhodium-catalyzed asymmetric hydrogenation of dehydro-α-amino acid derivatives, itaconic acids, and α-ketoesters. These air-stable ligands are readily prepared from cost-effective and non-pyrophoric intermediates.

METHOD OF PRODUCING OPTICALLY ACTIVE AMINO ACID DERIVATIVE

The present application relates to a method for producing an optically active α-amino acid derivative, comprising steps of reacting an α-haloester derivative represented by the general formula (1): of which alcohol part of the ester group is an optically active alcohol derivative, with an amine compound; then deprotecting the obtained compound; further carrying out an ester exchange reaction. According to the present invention method, it is possible to easily produce an optically active α-amino acid ester derivative which is useful as an intermediate for drugs with high selectivity.

The preparation of enantiomerically pure cyclopropylalanine

Single enantiomer cyclopropylalanine (>99.9% ee) and various derivatives were prepared using an asymmetric hydrogenation approach with a rhodium catalyst based on the methyl BoPhoz ligand. N-Boc cyclopropylalanine benzyl ester was the preferred derivative

Kinetic Resolution of Unnatural and Rarely Occuring Amino Acids: Enantioselective Hydrolysis of N-Acyl Amino Acids Catalyzed by Acylase I

Acylase I (aminoacylase; N-acylamino-acid amidohydrolase, EC 3.5.1.14, from porcine kidney and the fungus Aspergillus) is broadly applicable enzymatic catalyst for the kinetic resolution of unnatural and rarely occuring α-amino acids.Its enantioselectivity for the hydrolysis of N-acyl L-α-amino acids is nearly absolute, yet it accepts substrates having a wide range of structure and functionality.This paper reports the initial rates of enzyme-catalyzed hydrolysis of over 50 N-acyl amino acids and analogues, the stabilities of the enzymes in aqueous and aqueous/organic solutions, and the effects of different acyl groups and metal ions on the rates of enzymatic hydrolysis.Eleven α-amino and α-methyl α-amino acids were resolved on a 2-29-g scale.Crude L- and D-amino acid products had generally >90percent ee.The utility of resolved amino acids as chiral synthons was illustrated by the preparation of (R)- and (S)-1-butene oxide and the diastereoselective (cis:trans, 7-8:1) iodolactonization of three 2-amino-4-alkenoic acid derivatives.

CYCLOPROPYLALANINE, AN ANTIFUNGAL AMINO ACID OF THE MUSHROOM AMANITA VIRGINEOIDES BAS

Cyclopropylalanine, an antifungal amino acid, has been isolated from the mushroom Amanita virgineoides Bas.Its structure has been elucidated as (2s)-2-amino-3-cyclopropylpropionic acid, on the basis of the spectroscopic analysis and its synthesis from L-allylglycine.