Kofi Oppong's research while affiliated with University of Florida and other places
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Publications (4)
The synthesis of homochiral functionalized cyclohexylglycines and α-methylcyclohexylglycines via chelated Kazmaier–Claisen rearrangement is described. These were shown to be potent scaffolds for the development of MMP inhibitors.
A series of carboxylic acids was prepared based on cyclohexylglycine scaffolds and tested for potency as matrix metalloproteinase (MMP) inhibitors. Detailed SAR for the series is reported for five enzymes within the MMP family, and a number of inhibitors such as compound 18 display low nanomolar potency for MMP-2 and MMP-13, while selectively spari...
The synthesis of homochiral functionalized cyclohexylglycines and alpha-methylcyclohexylglycines via chelated Kazmaier-Claisen rearrangement is described. These were shown to be potent scaffolds for the development of MMP inhibitors.
Both enantiomers of dideoxyfluoroamino inositols (+)-9 and (−)-9 were synthesized from bromocyclohexadiene cis-diol 1 obtained by microbial oxidation of bromobenzene with toluene dioxygenase. Selective introduction of the amino group was achieved through SN2 displacement of triflates 7, 11. Fluorine was selectively introduced via trans-diaxial epox...
Citations
... 15,[19][20][21][22][23][24][25][26][27] Unfortunately, the lack of availability of most isomers has limited the extension of the research. In addition, many deoxygenated derivatives such as inosamines, conduramines and fluoroinositols are on demand for their study as glycosidase inhibitors 28,29 and for metabolic pathway research. [30][31][32][33] The chemoenzymatic approach to diverse cyclitols and cyclitol analogs via whole-cell oxidation of aromatics by toluene dioxygenase has been extensively explored by Hudlicky, [34][35][36][37][38][39][40][41][42][43][44][45] Nicolosi. ...
... Kazmaier's method is suitable for acyclic as well cyclic allylic esters [61,62] and can be applied to peptides [63]. From obtained results it is clear that the trimethylsilyl group is not only acting as a steric control element in a direction consistent with the transition state model, but also increasing the rate of this reaction. ...
... The key amino ester intermediates in this scheme were prepared in a few steps that included reduction of carboxylic acids a1-2, iodination of selected benzyl alcohols b3-4, followed by bromination to form d1-5 [38,39], coupling with the Schiff base g1 to yield the imino esters h1-6 [40,41], and deprotection under mild acidic conditions (i1-6) [41] (Schemes 3, and S1). These amino esters were coupled with the corresponding Boc protected amino acids m1-13 (Schemes 4, 5, S2, and S3) using standard COMU-mediated protocol to form dipeptides 3-7 and n1-13 (Schemes 5, and S3). ...
