497165-15-8

Basic information

• Product Name: (R)-BoroAla-(+)-Pinanediol
• Synonyms: (R)-BoroAla-(+)-Pinanediol
• CAS NO: 497165-15-8
• Molecular Formula: C12H22BNO2
• Molecular Weight: 223.11958
• Mol File: 497165-15-8.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-BoroAla-(+)-Pinanediol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-BoroAla-(+)-Pinanediol(497165-15-8)
• EPA Substance Registry System: (R)-BoroAla-(+)-Pinanediol(497165-15-8)

Safety Data

• Hazardous Substances Data: 497165-15-8(Hazardous Substances Data)

Usage

General Description

(R)-BoroAla-(+)-Pinanediol is a chiral organic compound that contains a boron atom and a carbinol group. It is commonly used as a chiral auxiliary in asymmetric synthesis, where it helps to induce stereochemical control in chemical reactions. The compound is often employed in the preparation of chiral building blocks and pharmaceutical intermediates. It has demonstrated utility in the construction of various natural products and biologically active molecules. Additionally, (R)-BoroAla-(+)-Pinanediol has been studied for its potential applications in catalysis and medicinal chemistry.

Upstream product

• 85167-12-0 (+)-pinanediol (1S)-1-chloro-1-ethaneboronate 
• 1313706-65-8 C₁₈H₃₈BNO₂Si₂ 
• 53404-49-2 2,3-trans-pinanediol 
• 132562-10-8 methylboronic acid pinanediol ester 

Downstream Products

• 919103-31-4 D-1-(aminoethyl)boronic acid pinanediol ester hydrochloride 

Relevant articles and documents

Characterization of d-boroAla as a novel broad-spectrum antibacterial agent targeting d-Ala-d-Ala ligase

d-boroAla was previously characterized as an inhibitor of bacterial alanine racemase and d-Ala-d-Ala ligase enzymes (Biochemistry, 28, 1989, 3541). In this study, d-boroAla was identified and characterized as an antibacterial agent. d-boroAla has activity against both Gram-positive and Gram-negative organisms, with minimal inhibitory concentrations down to 8μg/mL. A structure-function study on the alkyl side chain (NH2-CHR-B(OR')2) revealed that d-boroAla is the most effective agent in a series including boroGly, d-boroHomoAla, and d-boroVal. l-boroAla was much less active, and N-acetylation completely abolished activity. An LC-MS/MS assay was used to demonstrate that d-boroAla exerts its antibacterial activity by inhibition of d-Ala-d-Ala ligase. d-boroAla is bactericidal at 1× minimal inhibitory concentration against Staphylococcus aureus and Bacillus subtilis, which each encode one copy of d-Ala-d-Ala ligase, and at 4× minimal inhibitory concentration against Escherichia coli and Salmonella enterica serovar Typhimurium, which each encode two copies of d-Ala-d-Ala ligase. d-boroAla demonstrated a frequency of resistance of 8×10-8 at 4× minimal inhibitory concentration in S. aureus. These results demonstrate that d-boroAla has promising antibacterial activity and could serve as the lead agent in a new class of d-Ala-d-Ala ligase targeted antibacterial agents. This study also demonstrates d-boroAla as a possible probe for d-Ala-d-Ala ligase function.