1. Stereochemistry of Fully Acetylated Tetrahydropterins and Tetrahydroquinoxalines
- Author
-
Shingo Komatsu, Shizuaki Murata, Kazuhisa Ikemoto, and Ning Chen
- Subjects
Pharmacology ,chemistry.chemical_compound ,Quinoxaline ,Chemistry ,Stereochemistry ,Acetylation ,Organic Chemistry ,Cyclohexane conformation ,Structure based ,Pterin ,Analytical Chemistry ,Stereocenter - Abstract
Completely acetylated derivatives of naturally occurring tetrahydro-D-monapterin, (6R)-2-acetamido-6-[(1R,2R)-1,2,3-triacetoxypropyl]-5,8-diacetyl-5,6,7,8-tetrahydropteridin-4(3H)-one, show plus and minus CD signs at X 280 and 240 nm, respectively. Similar CD spectra are obtained on (2S)-1,4-diacetyl-1,2,3,4-tetrahydro-2-isopropylquinoxaline and (2S)-1,4-diacetyl-1,2,3,4-tetrahydro-2-isobutylquinoxaline but not on (25)-1,4-diacetyl-1,2,3,4-tetrahydro-2-methylquinoxaline nor on the 2-ethyl derivative. The similarity of their CD spectra is represented the same stereogenic structure based on the boat conformation confirmed by X-Ray crystallographic analyses.
- Published
- 2005
- Full Text
- View/download PDF