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“…Prior work demonstrated that the Pf A-M1 MAP had broad specificity, 47 however published structural data with bestatin demonstrated that the S1 pocket was lined with hydrophobic residues packing well around the P1 Phe sidechain (Fig.1). 46 Using this information we synthesized Bestatin derivatives using a series of α-hydroxy-β-amino acids consisting of aliphatic and aromatic side chains in increasing size and rigidity. To make use of these new α-hydroxy-β-amino acids, we synthesized a library on preloaded Wang resin wherein the second position (P1’) was fixed to a leucine, the amino acid yielding the most potent activity against PfA-M1 at this position.…”
Section: Resultsmentioning
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“…Prior work demonstrated that the Pf A-M1 MAP had broad specificity, 47 however published structural data with bestatin demonstrated that the S1 pocket was lined with hydrophobic residues packing well around the P1 Phe sidechain (Fig.1). 46 Using this information we synthesized Bestatin derivatives using a series of α-hydroxy-β-amino acids consisting of aliphatic and aromatic side chains in increasing size and rigidity. To make use of these new α-hydroxy-β-amino acids, we synthesized a library on preloaded Wang resin wherein the second position (P1’) was fixed to a leucine, the amino acid yielding the most potent activity against PfA-M1 at this position.…”
Section: Resultsmentioning
“…The crude diol 11a − h was selectively oxidized at the primary hydroxyl functionality to the α-hydroxy-β-amino acid 12 : 13 using TEMPO, NaClO 2 , and NaOCl in NaH 2 PO 4 . , Surprisingly, the secondary alcohol remained intact under the oxidation conditions (Scheme ). Given prior published data that the (2 S ,3 R ) diastereomers of bestatin are much more inhibitory than the corresponding (2 R ,3 R ) diastereomer, , the active (2 S ,3 R ) diastereomers 13a − h were purified by reverse phase HPLC. The 1 H NMR spectra of the 13a − h (2 S ,3 R ) diastereomers had the −NH (doublet) and −Boc (singlet) protons shift at similar ppm in all the examples under study in comparison to the phenyl derivative which is well studied (except for the diphenyl and n -propyl, where one diastereomer was exclusively formed).…”
Section: Resultsmentioning
“…These results indicated that apstatins as AP-P inhibitors could be efficacious in the treatment of various cardiovascular disorders by increasing levels of endogenously formed bradykinin [127]. The slow-binding inhibition mechanism was observed also for AP-P inactivated by dipeptidic inhibitors consisting of AHPA or AHMHA, respectively (Figure 6.6) [128]. Design of these compounds was based on the structure of bestatin and on the crystal structure of Escherichia coli AP-P in complex with apstatin.…”
Section: Inhibitors Of Aminopeptidasesmentioning
“…These compounds are β-turn inducers in the synthesis of peptides [4] and good enzyme inhibitors by themselves [5] as are several of their derivatives, such as deoxy-galactono-jirimicin derivatives [6,7,8]. Indeed, stereoselective synthesis of hydroxy-amino acids is a field that has been growing during the last decades because of the potential biological activity of some representatives of this class of compounds, mainly as enzyme inhibitors [5,9,10,11,12]. Particularly, conformationally constrained hydroxy-amino acids such as the hydroxylated pipecolic acids are very interesting target molecules [12,13].…”
Section: Introductionmentioning