Production of cis-1,2-dihydroxy-3-methylcyclohexa-3,5-diene (toluene cis glycol) by Rhodococcus sp. MA 7249.

J Biosci Bioeng

Department of Bioprocess, Merck Research Laboratories, RY 80Y-105, Merck and Co., PO Box 2000, Rayway, NJ 07065, USA.

Published: October 2005

AI Article Synopsis

  • A new method was developed to produce toluene cis glycol using a specific strain of Rhodococcus (MA 7249) lacking certain enzymes.
  • The produced toluene cis glycol exhibited optical rotations that confirmed its absolute configuration as (1S,2R).
  • When grown in a lab with toluene vapors, MA 7249 achieved a concentration of 18 g/l of toluene cis glycol in about 110 hours and also produced similar dihydrodiols from other compounds.

Article Abstract

An attractive method for producing cis-1,2-dihydroxy-3-methylcyclohexa-3,5-diene (toluene cis glycol) was developed employing a cis dihydrodiol dehydrogenase "deficient" strain of Rhodococcus (MA 7249). The toluene cis glycol produced was found to have optical rotations of [alpha]D25 = +25.8 (c 0.45, CH3OH) and +72.8 (c 0.42, CHCl3) which indicated an absolute configuration of (1S,2R) when compared with previously published values. When cultivated in laboratory fermentor in the presence of toluene vapors, MA 7249 reached a toluene cis glycol concentration up to 18 g/l in 110 h. Culture MA 7249 also accumulated cis (1S,2R) dihydrodiols from dihydronaphthalene, biphenyl, chlorobenzene, and styrene.

Download full-text PDF

Source

Publication Analysis

Top Keywords

toluene cis
16
cis glycol
16
cis-12-dihydroxy-3-methylcyclohexa-35-diene toluene
8
rhodococcus 7249
8
cis
6
toluene
5
production cis-12-dihydroxy-3-methylcyclohexa-35-diene
4
glycol
4
glycol rhodococcus
4
0
4

Similar Publications

Sodium salt of aryl sulfinic acid reacts with enynone in a different manner, yielding α-furyl sulfone and stereodefined vinyl sulfone in toluene and EtOH respectively in the presence of ZnCl. The salient features of this protocol include chemoselectivity, broad substrate scope, high efficiency, high yield, and easy purification. The synthetic utilities of the products are demonstrated by cycloaddition and cis-trans photoisomerization reactions.

View Article and Find Full Text PDF

Photo-responsive organogelator based on cholesterol incorporated sugar-azobenzene derivatives.

Carbohydr Res

December 2024

Department of Chemistry, School of Basic and Applied Sciences, Central University of Tamil Nadu (CUTN), Thiruvarur, 610 005, India. Electronic address:

In this report, the design and synthesis of cholesterol-based sugar azobenzene derivatives as photo-responsive organogelators have been carried out. The gel formation in different solvents was examined, and a minimum CGC of 0.5 % (w/v) was attained in toluene.

View Article and Find Full Text PDF

Cellulose Nanocrystal-in-Solvent Processing for Efficient One-Pot Upcycling of Commercial Polymeric PFAS.

ACS Appl Mater Interfaces

October 2024

Department of Materials Science and Engineering, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 08826, South Korea.

Upcoming regulations aim to ban per- and polyfluoroalkyl substances (PFAS), including commercial polymeric PFAS, or fluoropolymers, such as poly(tetrafluoroethylene) (PTFE) and poly(vinylidene fluoride) (PVDF), due to their environmental and toxicological impacts. However, fluoropolymers also provide crucial properties for clean energy transitions, and their regulation may hinder further technological advancements. Therefore, a facile one-pot recycling-upcycling strategy for fluoropolymers using inexpensive biomass, such as cellulose nanocrystals (CNCs), as absorbents and cocomponents for fluoro-functionalized composites could align with global sustainability goals and technological demands.

View Article and Find Full Text PDF

A novel Ir-catalyzed asymmetric hydrogenation protocol for the synthesis of chiral tetrahydroquinoxaline (THQ) derivatives has been developed. By simply adjusting the reaction solvent, both enantiomers of mono-substituted chiral THQs could be selectively obtained in high yields with excellent enantioselectivities (toluene/dioxane: up to 93% yield and 98% ee (); EtOH: up to 83% yield and 93% ee ()). For 2,3-disubstituted chiral THQs, the -hydrogenation products were obtained with up to 95% yield, 20 : 1 dr, and 94% ee.

View Article and Find Full Text PDF
Article Synopsis
  • - The research discusses the creation of a low-symmetry metallo-supramolecular barrel (UNMB) using an unsymmetrical tetratopic ligand and a protected Pd(ii) metal acceptor, deviating from typical symmetric assemblies.
  • - Different orientational isomers of the barrel were predicted, with experimental results indicating that the HHTT isomer was formed, verified through X-ray diffraction and H NMR analysis.
  • - UNMB has large openings and a hydrophobic interior, making it effective at encapsulating larger guests like fullerenes, with a preference for C₆₀ over C₇₀, enabling potential applications in separation processes.
View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!