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ChiroSolve Inc. 2065 Martin Ave, Suite 107, Santa Clara, CA 95050, USA ; Telephone: +1(408) 834-8597; Fax: +1(408) 351-7900; http://www.chirosolve.com

Vol 2, Issue 2   

CHIROSOLVE MONTHLY NEWSLETTER  

News You Can Use  

April 2011 Newsletter   

FEATURED PRODUCT

ChiroSolve EnantioPrep Solution

enantioprep_pic 4

FEATURED MOLECULE

 http://upload.wikimedia.org/wikipedia/commons/f/fa/Isocitric_acid.png 

Name: Isocitric acid
Image Source: http://upload.wikimedia.org/wikipedia/commons/f/fa/Isocitric_acid.png
Article: http://www.sciencedaily.com/releases/2008/02/080204111747.html

FEATURED ARTICLES

Chiral Building Blocks For New Pharmaceuticals Finally Available In Large Quantities (see more >>>)

Design of SMB Chiral Separations Using the
Concept of Separation Volume (see more >>>)

Revealing Atropisomer Axial Chirality in Drug Discovery (see more >>>)

detectiveDid you know this?

Bananas contain a natural chemical which can make a person happy. This same chemical is also found in Prozac.
 
A bee sting is acidic and a wasp sting is alkali. To treat a sting by one of these you should use the opposite type of chemical.
 
Some fullerenes (e.g. C76, C78, C80, and C84) are inherently chiral because they are D2-symmetric, and have been successfully resolved. Research efforts are ongoing to develop specific sensors for their enantiomers.
QUICK LINKS

ChiroSolve, Inc.

2065 Martin Ave, Suite 107

Santa Clara, Ca 95050, USA

 Phone: +1 (408) 834-8597;

Fax: +1 (408) 351-7900

E-Mail: info@chirosolve.com

Dear Chiral Chemistry Colleague,

Welcome back to ChiroSolve Monthly Newsletter, designed to bring insightful and timely information on trends and technology to innovators in Organic Chemistry.

In this issue, we would like to provide a more in-depth information about our NEW  ENANTIOPREP solution that identifies the optimal chiral separation candidates, defines step-by-step development method provides, and delivers up to 90% of theoretical yield of pure enantiomer; all in matter of days. Only 2 to 12 mmol of starting material is required; yet the devloped method is scalable to kilo quantities.

How to use ChiroSolve's EnantioPrep solution to get pure enantiomer in matter of days

EnantioPrep is designed to obviate the obstacles analytical chemists face during the elaborate process of diastereomeric crystallization. It offers cost efficient well-established method to identify a comprehensive set of chiral separation options, deliver pure enantiomer and define a scalable chiral separation. What sets EnantioPrep apart from other method development tools is the inclusion of ChiroSolv® Screening Kits that allow for 384 unique reagent combinations to identify optimum separation conditions. It is an extremely time and resource efficient approach to chiral resolution that allows analytical chemists to skip over the hard part of finding an optimal or scalable method to achieving an enantiopure product. This guided path to deliver pure enantiomer takes the guess work out of separation technology and engenders confidence that the methods are comprehensive and efficient.
 
EnantioPrep allows scientists to:

  • Quickly screen a racemate against comprehensive list of 384 resolving agent/solvent combination to identify all possible resolution conditions
  • Recover the used racemate and proceed to purify it until target purity is achieved
  • Define a step-by-step resolution method that can be scaled up to kilo quantities
                               enantioprepFlowcharts

The experiment involves 3 phases of work:

  1. Screening: Racemate is screened against 384 different combinations of resolving agents and solvents. When the combination of the racemate, resolving agent and solvent is heated together, diastereomeric salt of one enantiomer preferentially crystallizes out after cooling. The best combination of the reagent and solvent that offers the highest yield and enantiomeric enrichment for the target enantiomer is chosen for further enrichment.
  2. Recovery: After collecting all the material used during the screening process, which includes the racemate, resolving agents and the solvents, a “recovery solution” will separate out the racemate from the resolving agents to form of 2 liquid layers. A separatory funnel isolates the bottom layer from which the racemate is recovered (typically > 90% of the starting material).
  3. Purification: Using the selected separation condition, enantiomeric salt is obtained and further purified through 1 or more re-crystallization steps using the purification components until the optimal yield and purity is achieved. The end result is enriched enantiomer (maximum yield: about 35% of the total racemate used). Further, this step establishes how many re-crystallization steps are required to get the enantiomeric purity needed.

 

Chiral Building Blocks For New Pharmaceuticals Finally Available In Large Quantities

Journal reference:  Syntheses with a Chiral Building Block from the Citric Acid Cycle: (2R,3S)-Isocitric Acid by Fermentation of Sunflower Oil. Angewandte Chemie International Edition. doi: 10.1002/anie.200705000

Acknowledgement: The above story is reprinted (with editorial adaptations by ScienceDaily staff) from materials provided by Wiley-Blackwell

Through a combination of one biotechnological and one chemical step, and starting from sunflower oil, A. Giannis and co-workers from the University of Leipzig, have devised a large-scale synthesis of (2R-3S)-isocitric acid, the last intermediate in the citric acid cycle to become available in bulk quantities.

The citric acid cycle, one of the most important metabolic processes in our bodies, was formulated in 1937. Since then, all of the intermediates have been produced in multigram quantities—with one exception, (2R,3S)-isocitric acid. Athanassios Giannis and his team at the University of Leipzig have finally done it. Their process, a combination of one biotechnological and one chemical step, starts with sunflower oil, a renewable starting material. Isocitric acid and its derivatives thus become accessible on a kilogram scale.

In the citric acid cycle, acetyl CoA, formed in the breakdown of lipids, sugars, and amino acids, is used to produce energy that is biochemically available to an organism. Carbon dioxide and water are produced in this process. This reaction mechanism is named after one of the intermediate products, the anion of citric acid.

In nature, isocitric acid is always found with its isomer, citric acid. The difference between these two compounds is merely that the hydroxy group (-OH) is bound to a different carbon atom of each molecule. Large-scale separation of the two isomers has not been possible. A fermentative synthesis of the pure compound has also not worked.

Giannis team has now finally done it, thanks to a host of tiny helpers, the yeast Yarrowia lipolytica, which produces isocitrate from refined sunflower oil in previously unachievable yield and in a favorable isocitrate to citrate ratio. After the biomass is filtered out, electrodialysis is used to obtain the pure acids. The researchers use a trick to separate citric acid from isocitric acid: They use methanol to convert the compounds into the corresponding methyl esters. Why does this work? Whereas the citric acid ester crystallizes, the isocitric acid ester is a liquid. Separation then becomes child’s play.

Why was isocitric acid so important to these researchers? Isocitric acid is a compound with chiral centers—carbon atoms with four different groups bound to them. There are always two versions of a chiral center, one being the mirror image of the other. Smaller, easily accessible chiral compounds are useful building blocks for the synthesis of complex natural products and are interesting starting materials for the pharmaceutical industry. Isocitric acid makes available a new assortment of such chiral building block. (see more >>>)

 
    Copyright 2010 Chirosolve, Inc. All rights reserved.                                                            Vol2, Issue2 April 2011 Newsletter




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