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Stereocontrolled synthesis of deuterated phenylalanine derivatives through manipulation of an N -phthaloyl protecting group for the recall of stereochemistry. Application in the study of phenylalanine ammonia lyase

Date

2001

Authors

Easton, Christopher
Fryer, Nicholas
Kelly, James
Kociuba, Katherine

Journal Title

Journal ISSN

Volume Title

Publisher

ARKAT Foundation

Abstract

The enantiomers of [2-2(H1]phenylalanine and all four stereoisomers of [2,3-2H2]phenylalanine) have been prepared from (S)-phenylalanine through the introduction of a chiral centre onto an N-phthaloyl protecting group for the recall of stereochemistry. Studies of the interaction of these labelled phenylalanines with (S)-phenylalanine ammonia lyase show that both the C-2 and C-3 hydrogens of the product trans-cinnamate undergo exchange with solvent in the presence of the enzyme. The mechanistic implications of this observation are discussed.

Description

Keywords

Keywords: cinnamic acid; hydrogen; n phthaloyl 4 aminobutyric acid; phenylalanine ammonia lyase; phenylalanine derivative; solvent; article; enantiomer; stereochemistry; stereoisomerism; structure analysis

Citation

Source

ARKIVOC

Type

Journal article

Book Title

Entity type

Access Statement

License Rights

DOI

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