Antibodies were raised against an analogue of one of the photo products (the head-to-head syn dimer) of trans methyl p- nitrocinnamate. When a solution of the monomer was irradiated in the presence of these antibodies, the product formed preferentially was the one against which antibodies had been raised. Photoisomerization of the monomer, the major photochemical reaction in the absence of antibodies, was greatly suppressed. Thus, the antibody combining site serves as a template for promoting selectively one reaction. The structure and absolute stereochemistry of (Z) (+)-2-bromocycloundec-2-enyl camphanate, a compound prepared as part of a study of the relationship between the chiroptical properties of the corresponding p-bromobenzoate esters and the configuration and conformation of medium-ring allylic esters, was determined in an X-ray crystallographic study. In the course of the same study, the structure and absolute stereochemistry of (E) (-)-2-cyclodecenyl camphanate was also determined by X-ray crystallography. As part of our work on asymmetric synthesis we developed a general method of resolving polycyclic aromatic alcohols, metabolites of polycyclic aromatic hydrocarbons. This method was used to prepare (+)-l-acenaphthenol, a substrate used to analyze several dehydrogenases. The absolute stereochemistry of the camphanate ester of the alcohol was elucidated by an X-ray crystallographic study. Chiral samples of beta-methylaminoalanine (BMAA) (a reported neurotoxin) and of an 15N labeled sample were prepared utilizing an enzymic resolution. The metabolism of the reported neurotoxin and as well as its pharmacology are being investigated by Dr. Markey et al. in NIMH (see Z01-MH-00279-05-LCS).
