28624-52-4

Basic information

• Product Name: Cyclopropanecarboxylic acid, 2,2-dimethyl-, (R)-
• CAS NO: 28624-52-4
• Molecular Formula: C6H10O2
• Molecular Weight: 114.144
• Mol File: 28624-52-4.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Cyclopropanecarboxylic acid, 2,2-dimethyl-, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopropanecarboxylic acid, 2,2-dimethyl-, (R)-(28624-52-4)
• EPA Substance Registry System: Cyclopropanecarboxylic acid, 2,2-dimethyl-, (R)-(28624-52-4)

Safety Data

• Hazardous Substances Data: 28624-52-4(Hazardous Substances Data)

Upstream product

• 110919-15-8 (4R,6R)-2-((R)-2,2-Dimethyl-cyclopropyl)-4,6-dimethyl-[1,3]dioxane 
• 1740-74-5 1,1-diethoxy-3-methyl-2-butene 
• 167482-50-0 1,2-O-Isopropylidene-3-O-(p-phenylbenzyl)-4,5-O-<(1'R)-3'-methyl-2'-buten-1'-yl>-β-D-fructopyranose 
• 107-86-8 3,3-dimethyl acrylaldehyde 
• 110919-09-0 (4R,6R)-4,6-Dimethyl-2-(2-methyl-propenyl)-[1,3]dioxane 
• 1759-55-3 (RS)-2,2-dimethylcyclopropanecarboxamide 

Downstream Products

• 50675-57-5 dl-2,2-dimethylcyclopropane-1-carboxylic acid chloride 

Relevant articles and documents

Industrial production of S-2,2-dimethylcyclopropanecarboxamide with a novel recombinant R-amidase from Delftia tsuruhatensis

R-Stereoselective amidase, a key enzyme responsible for the formation of chiral center of cilastatin, has been cloned from Delftia tsuruhatensis and expressed in Escherichia coli under T7 promoter. This recombinant amidase exhibits strict R-selectivity towards 2,2-dimethylcyclopropanecarboxamide (DMCPCA). The amidase activity of the engineered E. coli strain reached 2963 U/L in a 5-L bioreactor, which was 8.27 times higher than that of D. tsuruhatensis, and was further increased to 5255 U/L in a 100-L bioreactor. Using cell-free extract prepared from 1 kg (wet cell weight) of recombinant E. coli cells as catalyst, 60 kg of R,S-DMCPCA was resolved into S-DMCPCA (28.6 kg) and R-2,2-dimethylcyclopropanecarboxylic acid (R-DMCPCS 31.7 kg) in 18 h, and the enantiomeric excess (ee) value of S-DMCPCA reached 99.32%. During the purification process, 24.6 kg of S-DMCPCA was eluted from adsorption resin HZ801 with 80% (v/v) acetone, and then 20.5 kg of pure S-DMCPCA was obtained after concentration and crystallization, corresponding to a total yield of 34.2% from R,S-DMCPCA. Therefore, the industrial production process of S-DMCPCA was successfully established using recombinant R-amidase from D. tsuruhatensis.

Production of L-tryptophan by enantioselective hydrolysis of d,l-tryptophanamide using a newly isolated bacterium

Bacterial strain ZJB-09211 capable of amidase production has recently been isolated from soil samples. The strain is able to asymmetrically hydrolyze l-tryptophanamide from d,l-tryptophanamide to produce l-tryptophan in high yield and with excellent stereoselectivity (enantiomeric excess > 99.9 %, and enantiomeric ratio > 200). Strain ZJB-09211 has been identified as Flavobacterium aquatile based on the cell morphology analysis, physiological tests, and the 16S rDNA sequence analysis. Optimization of the fermentation medium led to an about six-fold increase in the amidase activity of strain ZJB-09211, which reached 501.5 U L-1. Substrate specifity and stereoselectivity investigations revealed that amidase of F. aquatile possessed a broad substrate spectrum and high enantioselectivity.

Asymmetric Cyclopropanation Using New Chiral Auxiliaries Derived from D-Fructose

Acetals of α,β-unsaturated aldehydes with 3-O-alkylated derivatives of 1,2-O-isopropylidene-β-D-fructopyranose and 1,2-O-isopropylidene-β-D-psicopyranose, which are readily available from D-fructose, were cyclopropanated with Et2Zn and CH2I2 with good diastereoselectivity.The effects of structure of the acetals on enantioselectivity were examined.