Appendixes Look at the Scope Notes in the Major Concepts Branch of the Authority File to see which Major Concepts were previously represented by Concept Codes. MAJOR CONCEPTS: Hematology Human Medicine, Medical Sciences Methods and Techniques; Molecular Genetics Biochemistry and Molecular Biophysics ; BIOSYSTEMATIC NAMES: Viruses--Microorganisms ORGANISMS: adeno-associated virus vector viron Viruses ; -recombinant BIOSYSTEMATIC CLASSIFICATION SUPER TAXA ; : Microorganisms; Viruses DISEASES: hemophilia--blood and lymphatic disease, genetic disease, therapy METHODS & EQUIPMENT: DNA molecule muscle cell delivery-molecular genetic method; gene therapy--recombinant gene expression, therapeutic method; in vivo recombinant adenoassociated virus muscle tissue injection--administration method ALTERNATE INDEXING: Hemophilia A MeSH ; CONCEPT CODES: 03502 Genetics and Cytogenetics-General 12512 Pathology, General and Miscellaneous-Therapy 1971- ; 15006 Blood, Blood-Forming Organs and Body FluidsBlood, Lymphatic and Reticuloendothelial Pathologies 31500 Genetics of Bacteria and Viruses, because detrol la overnight.
Amano R derived from Penicillium roquefortii, which exhibited a selectivity sufficient for preparative application E 19 ; . Interestingly, this latter enzyme is only rarely used in preparative biotransformations. Compound 10a is clearly the optimal substrate in this series, since it was converted by several enzymes in acceptable lipase Amano AH, E 27 ; or even good selectivities lipases from Candida rugosa and Mucor miehei, E 49 ; . Interestingly, Mucor sp. lipase and porcine liver esterase showed an opposite enantiopreference to all other lipases. In addition, for 10a medium engineering proved to be a powerful tool for selectivity enhancement. Thus, by switching from aqueous diisopropyl ether to aqueous toluene, selectivities increased considerably: for lipase AH E 427 ; , for lipase from Candida rugosa E 4.249 ; , and for Mucor sp. lipase E 1.449 ; . The optical yields of substrates and products were determined by HPLC enantioseparation using a Chiralcel OD-H column enantiomerically enriched acids 9ac were converted into the corresponding methyl esters by treatment with diazomethane prior to analysis ; .10 In order to establish the enantiopreference in the biocatalytic experiments the absolute configuration of these methyl esters was determined by comparison of their CD spectra with reference samples of known absolute configuration as we have detailed elsewhere.23 Despite the acceptable selectivities for some of the examples shown in Table 1, the corresponding conversion rates for these cases were too low 110% ; to allow any meaningful preparative resolution experiments. At this point we had to consider an alternative activation approach. The amide functionality present in dihydropyrimidones of the DHPM type in principle also allows the attachment of an acyloxymethyl residue at the N3 position i.e. structure 12 ; functioning as a "molecular handle". One apparent advantage of this set-up would be that the distance of the enzymatically cleavable ester functionality from the chiral center is reduced by two carbon atoms i.e. from 6 to 4 bonds ; , which should lead to improved selectivities. Furthermore, enantioselective cleavage of the ester would lead to a hemiaminal which is expected to readily undergo chemical hydrolysis directly to the corresponding enantiopure N3-unsubstituted DHPM, thereby making further manipulations i.e. of the C5 carboxy functionality ; unnecessary. With this in mind we have prepared the corresponding N3-POM-activated DHPMs 12ac as shown in Scheme 4 following standard procedures. Unfortunately, preliminary enzymatic screens using most of the lipases indicated in Table 1 soon made evident that DHPMs 12ac were rather resistant towards enzymatic hydrolysis, despite medium engineering and changes in reaction temperature. In order to increase conversion rates we have therefore synthesized some of the corresponding less bulky acetoxymethyl analogs, initially employing acetoxymethyl chloride instead of POM-Cl in the alkylation step. At the same time we also considered changing the N1-methyl substituent 4384 J. Chem. Soc., Perkin Trans. 1, 2000, 43824389.
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