The strategy of combined site directed mutagenesis and chemical modification creates chemically modified mutants (CMMs) with greatly broadened substrate specificities. We have previously reported that the CMMs of subtilisin Bacillus lentus (SBL) are efficient catalysts for the coupling of both Land D-amino acids. We now report that these powerful catalysts also allow amide bond formation betwee...

Molecular quantum similarity was studied for a set of peptide isosteres analyzed before by Boon et al. (Chemical Physics Letters, 1998, 295 122). Overlap and Coulomb similarity measures in coordinate space were calculated using the TGSA (Topo-Geometrical Superposition Algorithm) algorithm for the alignment of molecules instead of the one used in the previous work, and a comparison between the s...

The known procedures for the conversion of alkenylstannanes into the corresponding fluoroalkenes suffer from largely variable yields and a limited compatibility with functional groups; most notably, protodestannation becomes a serious issue whenever protic sites are present in the substrate. Outlined in this paper is a convenient alternative with a much improved application profile, which is la...

Bioisosteres are atoms or group of molecules that fit the broadest definition for isosteres. They have chemical and physical similarities thus producing broadly similar biological properties. Many heterocycles, when appropriately substituted exhibits bioisosterism. Bioisosterism represents an approach used by the medicinal chemist for the rational modification of lead compounds into safer and m...

Amidine-type peptide bond isosteres were designed based on the substitution of the peptide bond carbonyl (C=O) group with an imino (C=NH) group. The positively-charged property of the isosteric part resembles a reduced amide-type peptidomimetic. The peptidyl amidine units were synthesized by the reduction of a key amidoxime (N-hydroxyamidine) precursor, which was prepared from nitrile oxide com...

The first example of catalytic B-H activation of azaborines leading to a new family of stilbene derivatives through dehydrogenative borylation is reported. Ten 1,2-azaborine-based BN isosteres of stilbenes have been synthesized using this method, including a BN isostere of a biologically active stilbene. It is demonstrated that BN/CC isosterism in the context of stilbenes can lead to significan...