✦ LIBER ✦
Biosynthesis of Natural Products with a PC Bond, X. Incorporation ofD-[1-2H1]Glucose into 2-Aminoethylphosphonic Acid inTetrahymena thermophila and into Fosfomycin inStreptomyces fradiae. — the Stereochemical Course of a Phosphoenolpyruvate Mutase-Catalyzed Reaction
✍ Scribed by Hammerschmidt, Friedrich ;Kählig, Hanspeter
- Book ID
- 102368495
- Publisher
- John Wiley and Sons
- Year
- 1992
- Tongue
- English
- Weight
- 257 KB
- Volume
- 1992
- Category
- Article
- ISSN
- 0947-3440
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✦ Synopsis
Abstract
2‐Aminoethylphosphonic acid and fosfomycin produced on feeding D‐[1‐^2^H~1~]glucose to Tetrahymena thermophila and Streptomyces fradiae, respectively, indicate that the phosphoenolpyruvate mutase catalyzes the stereospecific transfer of the phospho group of (Z)‐phosphoenol‐[3‐^2^H~1~]pyruvate from oxygen to carbon from the si face. ^2^H‐NMR spectroscopy was used to determine the configuration at C‐1 of biosynthetically formed 2‐amino‐[1‐^2^H~1~]ethylphosphonic acid after derivatization with (—)‐camphanoyl chloride and diazomethane.