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The Stereochemistry of Biosythetic Phenylserine

Undergraduate #152
Discipline: Chemistry and Chemical Sciences
Subcategory: Biochemistry (not Cell and Molecular Biology and Genetics)

Shahrazad Polk - Texas Southern University
Co-Author(s): Prakash Shee and Kevin D. Walker, Michigan State University, East Lansing, MI



Phenylserine is classified as a β-hydroxy-α-amino acid, which generally are the building blocks of many important medicines, such as Lysobactin, L-DOPS, and Vancomycin. Non-stereoselective synthetic methods make four stereoisomers of Phenylserine; L-erythro-, d-erythro-, L-threo-, and D-threo-Phenylserine. Here, we look to use a stereo controlled biosynthetic approach to make Phenylserine. Thus, identifying the stereochemistry of the product is pertinent. What is the stereochemistry of Phenylserine made biosynthetically by our TcPAM? If more than one stereoisomer is made, can we separate and characterize the stereochemistry of the isomer? Medicines that contain a Phenylserine building block typically use the L-isomer. To identify these isomers we used L-threonine aldolase.

Funder Acknowledgement(s): National Science Foundation (NSF)

Faculty Advisor: Kevin D. Walker, walker@chemistry.msu.edu

Role: I tested the methods for determining the stereochemistry of biosythetic phenylserine.

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This material is based upon work supported by the National Science Foundation (NSF) under Grant No. DUE-1930047. Any opinions, findings, interpretations, conclusions or recommendations expressed in this material are those of its authors and do not represent the views of the AAAS Board of Directors, the Council of AAAS, AAAS’ membership or the National Science Foundation.

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