Abstract
Pyridoxamine has been attached to the primary side and to the secondary side of β-cyclodextrin; the resulting compounds convert a-keto acids to amino acids with substrate selectivity and some stereoselectivity. Pyridoxamine has also been attached to a synthetic macrocycle; the attached binding group showed substrate selectivity. Chains carrying catalytic basic groups have been attached to pyridoxamine; appropriate systems catalyze the prototropic rearrangement characteristic of transamination. A catalyzed HCl elimination involving chloropyruvic acid was also observed. A tetrahydroquinoline system related to pyridoxamine was synthesized to permit the stereochemically defined placement of a basic catalytic group. This converted keto acids to amino acids with good stereoselectivity for the formation of optically active products.
Original language | English |
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Pages (from-to) | 1969-1979 |
Number of pages | 11 |
Journal | Journal of the American Chemical Society |
Volume | 108 |
Issue number | 8 |
DOIs | |
State | Published - 1 Jan 1986 |
Externally published | Yes |
ASJC Scopus subject areas
- Catalysis
- General Chemistry
- Biochemistry
- Colloid and Surface Chemistry