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1999•Angewandte Chemie International EditionRequires access

Total Synthesis of the Marine Natural Product 7‐Deoxy‐okadaic Acid: A Potent Inhibitor of Serine/Threonine‐Specific Protein Phosphatases

Amy B. Dounay, Rebecca A. Urbanek, Steven F. Sabes, Craig J. Forsyth

Open publisher page 38 citations

Abstract

A small change to the structure of okadaic acid (1), the omission of the single hydroxy group at C7, facilitated substantially the first total synthesis of the derivative 7-deoxyokadaic acid (2). The conformation of 2 is in agreement with that of 1 and this minimal structural variation has been reported previously to have little effect on the inhibitory activity towards the serine/threonine-specific protein phosphatases PP-1 and PP-2A.

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What this paper is about

A small change to the structure of okadaic acid (1), the omission of the single hydroxy group at C7, facilitated substantially the first total synthesis of the derivative 7-deoxyokadaic acid (2). The conformation of 2 is in agreement with that of 1 and this minimal structural variation has been reported previously to have little effect on the inhibitory activity towards the serine/threonine-specific protein phosphatases PP-1 and PP-2A.

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Available abstract

A small change to the structure of okadaic acid (1), the omission of the single hydroxy group at C7, facilitated substantially the first total synthesis of the derivative 7-deoxyokadaic acid (2). The conformation of 2 is in agreement with that of 1 and this minimal structural variation has been reported previously to have little effect on the inhibitory activity towards the serine/threonine-specific protein phosphatases PP-1 and PP-2A.

Key concepts: Okadaic acid, Threonine, Serine, Chemistry, Natural product, Phosphatase, Biochemistry, Total synthesis

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Total Synthesis of the Marine Natural Product 7‐Deoxy‐okadaic Acid: A Potent Inhibitor of Serine/Threonine‐Specific Protein Phosphatases — Research Paper | ScholarLens