Peptide Inhibitors of Aspartic Proteinases with Hydroxyethylene Isostere Replacement of Peptide Bond. II. Preparation of Pseudotetrapeptides Derived from Diastereoisomeric 5-Amino-2-benzyl-4-hydroxy-6-phenylhexanoic Acids

[img]PDF - Authorized users only
Language: English
51Kb
Title:Peptide Inhibitors of Aspartic Proteinases with Hydroxyethylene Isostere Replacement of Peptide Bond. II. Preparation of Pseudotetrapeptides Derived from Diastereoisomeric 5-Amino-2-benzyl-4-hydroxy-6-phenylhexanoic Acids
Creators:
Litera, Jaroslav
Weber, Jan
Křížová, Ivana
Pichová, Iva
Konvalinka, Jan
Fusek, Martin
Souček, Milan
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 63, 4, pp. 541-548
Uncontrolled Keywords:Pseudopeptides, HIV-1 proteinase, <i>Candida</i> sp. proteinases, Peptidomimetics, Aspartic proteinase inhibitors

Abstract

Twelve pseudotetrapeptides, Boc-NHCH(CH<sub>2</sub>Ph)CH(OH)CH<sub>2</sub>CH(CH<sub>2</sub>Ph) CO-Xaa-Phe-NH<sub>2 </sub><strong>9-11</strong>, were prepared by [(benzotriazol-1-yl)oxy]tris(dimethylamino)phosphonium hexafluorophosphate-mediated couplings of diastereoisomeric <i>O</i>-silylated (2<i>R </i>or 2<i>S</i>,4<i>R </i>or 4<i>S</i>,5<i>S</i>)-2-benzyl-5-(<i>tert</i>-butoxycarbonyl)amino-4-hydroxy-6-phenylhexanoic acids <strong>1</strong> with dipeptides H-Xaa-Phe-NH<sub>2 </sub>(Xaa = Gln, Glu(OBzl) or Ile) <strong>3-5</strong>, followed by <i>O</i>-deprotection. Pseudotetrapeptides <strong>9-11</strong> were tested for inhibition of aspartic proteinases secreted by <i>Candida albicans</i> and <i>C. tropicalis</i>. The level of inhibition of both yeast proteinases was very low, contrasting with the nanomolar IC<sub>50 </sub>values obtained for inhibition of HIV-1 proteinase.

Title:Peptide Inhibitors of Aspartic Proteinases with Hydroxyethylene Isostere Replacement of Peptide Bond. II. Preparation of Pseudotetrapeptides Derived from Diastereoisomeric 5-Amino-2-benzyl-4-hydroxy-6-phenylhexanoic Acids
Creators:
Litera, Jaroslav
Weber, Jan
Křížová, Ivana
Pichová, Iva
Konvalinka, Jan
Fusek, Martin
Souček, Milan
Uncontrolled Keywords:Pseudopeptides, HIV-1 proteinase, <i>Candida</i> sp. proteinases, Peptidomimetics, Aspartic proteinase inhibitors
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:63
Number:4
Page Range:pp. 541-548
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19980541UNSPECIFIED
ID Code:1320
Item Type:Article
Deposited On:06 Feb 2009 17:08
Last Modified:06 Feb 2009 16:08

Citation

Litera, Jaroslav; Weber, Jan; Křížová, Ivana; Pichová, Iva; Konvalinka, Jan; Fusek, Martin; Souček, Milan (1998) Peptide Inhibitors of Aspartic Proteinases with Hydroxyethylene Isostere Replacement of Peptide Bond. II. Preparation of Pseudotetrapeptides Derived from Diastereoisomeric 5-Amino-2-benzyl-4-hydroxy-6-phenylhexanoic Acids. Collection of Czechoslovak Chemical Communications, 63 (4). pp. 541-548. ISSN 0010-0765

Repository Staff Only: item control page