Oxaprostaglandin Explained

An oxaprostaglandin is a type of prostaglandin with one carbon atom replaced by an oxygen atom. These are found in nature and have also been produced synthetically.

Medical uses

A 13-oxaprostaglandin analogue has been shown to treat glaucoma and ocular hypertension.[1] The 11-oxa prostaglandin analogue AL-12182 1 has potent topical ocular hypotensive activity.[2] 7-Oxa-13-prostynoic acid promotes erythrocyte lysis and dissolution of erythrocyte membranes.[3]

Synthesis

11-Oxaprostaglandin f2α and 11-oxaprostaglandin f2β have been synthesized from D-glucose.[4]

Notes and References

  1. Feng. Zixia. Hellberg, Mark R.. Sharif, Najam A.. McLaughlin, Marsha A.. Williams, Gary W.. Scott, Daniel. Wallace, Tony. Discovery of 13-oxa prostaglandin analogs as antiglaucoma agents: Synthesis and biological activity. Bioorganic & Medicinal Chemistry. 1 January 2009. 17. 2. 576–584. 10.1016/j.bmc.2008.11.070. 19101156.
  2. Fox. Martin E.. Jackson, Mark. Lennon, Ian C.. McCague, Raymond. A Convergent Synthesis of the 11-Oxa Prostaglandin Analogue AL-12182. The Journal of Organic Chemistry. 1 February 2005. 70. 4. 1227–1236. 10.1021/jo048035v. 15704955.
  3. Swislocki. Norbert I.. Tierney, Joan. Ritterstein, Susan. Disruption of human erythrocytes with 7-oxa-13-prostynoic acid. Prostaglandins. 1 September 1974. 7. 5. 401–410. 10.1016/0090-6980(74)90105-1. 4214491.
  4. Book: Hanessian, Stephen. Total Synthesis of Natural Products: The 'Chiron' Approach. 1983. Pergamon press. 978-0-08-029247-2. 63.

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