Synthesis of human ultraviolet filter compounds: O-β-D- glucopyranosides of 3-hydroxykynurenine and 2-amino-3-hydroxy-γ- oxobenzenebutanoic acid

Michael K. Manthey, Joanne F. Jamie*, Roger J W Truscott

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)

Abstract

The role of endogenous tryptophan-derived UV filters in aging lenses and in human cataract is becoming increasingly important. The two major UV filters found in the lenses of primates, the O-β-D-glucopyranosides of 3- hydroxykynurenine and 2-amino-3-hydroxy-γ-oxobenzenebutanoic acid, 1 and 2, were synthesized from the common benzoyl acrylate precursor 2-amino-3- hydroxybenzoylacrylic acid 10. Synthesis of compound 3, the α-N-acetyl derivative of 1, was achieved using coupling of 2-nitro-3- benzyloxyacetophenone 4 with the sodium salt of diethyl acetamidomalonate as a key step. This is the first reported synthesis of the lenticular glucopyranoside 2 and the N-acetyl compound 3.

Original languageEnglish
Pages (from-to)3930-3933
Number of pages4
JournalJournal of Organic Chemistry
Volume64
Issue number11
DOIs
Publication statusPublished - 28 May 1999
Externally publishedYes

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