Pteridine, LXVIII. Überführung von Biopterin in Sepiapterin und absolute Konfiguration des Sepiapterins
✍ Scribed by Sepiapterins, Konfiguration Des ;Pfleiderer, Wolfgang
- Publisher
- Wiley (John Wiley & Sons)
- Year
- 1979
- Tongue
- English
- Weight
- 304 KB
- Volume
- 112
- Category
- Article
- ISSN
- 0009-2940
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✦ Synopsis
Pteridines, LXVIII. Transformation of Biopterin into Sepiapterin and Absolute Configuration of Sepiapterin
A new synthesis of the Drosophila pigment sepiapterin (10) has been found in the pH‐dependent autoxidation of 5,6,7,8‐tetrahydrobiopterin (1). Most sepiapterin is formed at pH4 leading to a 20% yield. Autoxidation of 1 at pH 7.5 caused a more severe degradation with preferential formation of 7,8‐dihydroxanthopterin (11). The absolute configuration of the chiral center in 10 has been established and this natural product characterized as 6‐[(S)‐lactoyl]‐7,8‐dihydropterin. The photochemical degradation of 10 yielded pterin‐6‐carboxylic acid (5).