A Method for Late Introduction of the (8R)-Hydroxyl Group in Carbapenem beta-Lactam Antibiotic Synthesis

Case ID:
C10954
C10954: Enzymes and Methods for Improved Syntheses of Carbapenem Beta-Lactam Antibiotics

Value Proposition:





• Regio- and stereospecific introduction of the (8R)-hydroxyl group late in a chemoenzymatic production process

• Simpler, more chemically robust starting materials can be used from the outset allowing more vigorous reaction conditions in subsequent steps

• Simpler, cheaper, and more robust routs of syntheses of carbapenem Beta-lactam antibiotics.

Technical Details:

Background

Carbapenem antibiotics are highly potent, broad spectrum compounds that are resistant to most Beta-lactamases. Their sales represent an estimated $15 billion in the US, and as a family they constitute more than 65% of the global antibiotic market. Commercially useful carbapenem Beta-lactam antibiotics are currently produced by a fully synthetic method which is complex and expensive. Technology

JHU scientists have isolated, synthesized, and characterized enzymes that catalyze critical steps (introduction of the (8R)-hydroxyl group) in the synthesis of carbapenem Beta-lactam antibiotics. These enzymes are highly efficient, and provide for the development of simpler, cheaper, and more robust routes of syntheses for this class of compounds. The invention enables introduction of the (8R)-hydroxyl group late in a chemo enzymatic production process of clinically-used carbapenem Beta-lactams antibiotics. Late introduction of this function means that simpler, more chemically robust starting materials can be used from the outset allowing more vigorous reaction conditions in subsequent steps and





Looking for Partners:

Efficient production of carbapenum Beta-lactam antibiotics capable of overcoming resistance mechanisms.



Patent Status: US patent granted

Publications/Associated Cases: US 9,139,588; EP 2513112; CA 2783962;  PMC2821876

Bodner MJ, Phelan RM, Freeman MF, Li R, Townsend CA. Non-heme iron oxygenases generate natural structural diversity in carbapenem antibiotics. J Am Chem Soc. 2010 Jan 13; 132(1):12-3.
Patent Information:
Title App Type Country Serial No. Patent No. File Date Issued Date Expire Date Patent Status
METHOD FOR LATE INTRODUCTION OF THE (8R)-HYDROXYL GROUP IN CARBAPENEM BETA-LACTAM ANTIBIOTIC SYNTHESIS PCT: Patent Cooperation Treaty United States 13/515,114 9,139,588 10/29/2012 9/22/2015 12/13/2030 Granted
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For Information, Contact:
Heather Curran
hpretty2@jhu.edu
410-614-0300
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