Antibody-catalyzed double stereoselection in fluorinated materials

Efficient and Selective P‐nitrophenyl‐ester‐hydrolyzing Antibodies Elicited by a P‐nitrobenzyl Phosphonate Hapten

“…Antibody D2.3 is the best catalyst for hydrolysis of 2b among the clones obtained from this fusion (Tawfik et al, 1993b); it exhibits a significant rate enhancement (kLdtlkuncat = l.lXIOs; k,.,,lK, = 185 s-' M-') and multiple turnovers (~3 0 0 ) . In comparison with all other reported catalytic antibodies that catalyze the hydrolysis of similar ester substrates, namely, substrates having benzyl (Janda et al, 1989;Miyashita et al, 1993) or alkyl (Pollack et al, 1989;Landry et al, 1993;Nakatani et al, 1994;Campbell et al, 1994;Tanaka et al, 1996;Yang et al, 1996) leaving groups [including an ally1 (Ikeda et al, 1991) or a 2-fluoroalkyl ester (Kitazume et al, 1991)], D2.3 exhibits both the highest rate acceleration (k,,,lk,,,,,) and also the highest kcatlKM.…”

“…Since that time, a large number and variety of anti-phosphonate, ester (and carbonate-ester) hydrolyzing antibodies have been reported (Tramontano et al, 1988;Durfor et al, 1988;Janda et al, 1988Janda et al, , 1989Pollack et al, 1989;Tawfik et al, 1990;Ikeda et al, 1991;Kitazume et al, 1991;Fujii et al, 1991 ;Miyashita et al, 1993;Landry et al, 1993;Ohkubo et al, 1993;Nakatani et al, 1993Nakatani et al, , 1994Guo et al, 1994;Campbell et al, 1994;Suga et al, 1994;Li et al, 1995;Stahl et al, 1995;Tanaka et al, 1996;Wentworth et al, 1996;Yang et al, 1996). Polyclonal anti-phosphonate, ester-hydrolyzing antibodies have respectively.…”

Catalytic antibodies: prospects for the use in organic synthesis

“…The diastereomeric alcohols 22a were resolved by the hydrolysis of their phenylacetates 22b catalysed by the catalytic antibodies raised against the haptens 23 having syn-and anticonfigurations. 22 The catalytic antibody against the syn-isomer of 23 hydrolysed the syn-isomer of 22b to yield the alcohol with optical purity 99% (the degree of hydrolysis was 49%), while CA against the antiisomer of 23 hydrolysed the anti-isomer of 22b with the same high degree of purity. The resolution of the alcohols HOCH(R F )C(-F)(Alk)CH 2 OBn, which differed from compounds 22a in the length of the aliphatic chain (Et, Pr and Bu substituents instead of the methyl substituent), occurred in a similar way.…”

“…The resolution of all the four diastereomers of the amino alcohols 24a from a mixture of their phenylacetates 24b using a set of CA raised against the diastereomeric haptens 25 has been reported. 22 An attempt was undertaken to obtain a catalytic antibody of the esterase type that would efficiently cleave one of the most hazardous narcotic agents, viz., cocaine, and to use it in the design of a medicinal drug that would not merely bind the narcotic but also decompose it into nontoxic components. Hydrolysis of cocaine (26) leads to its degradation into the nontoxic ecgonine methyl ester (27) and benzoic acid (Scheme 2).…”

A Facile Synthesis of New L‐Proline‐Based Trifluoromethyl Oxazole Derivatives Using Microwave Irradiation and Conventional Method

“…Recently, organofluorine compounds have attracted huge interest in the pharmaceutical and agrochemical industries . In particular, trifluoroacetimidoyl chloride‐substituted molecules have become a subject of intense investigation , because fluorinated building blocks exhibit interesting biological activity . Trifluoromethylated compounds have attracted considerable attention due to the influence of fluorine atoms, they often furnish organic molecules with unique properties that cannot be attainted using any other element .…”