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 language | English |
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Pages (from-to) | 3930-3933 |
Number of pages | 4 |
Journal | Journal of Organic Chemistry |
Volume | 64 |
Issue number | 11 |
DOIs | |
Publication status | Published - 28 May 1999 |
Externally published | Yes |