Peptide Inhibitors of Aspartic Proteinases with Hydroxyethylene Isostere Replacement of Peptide Bond. I. Preparation of Four Diastereoisomeric (2R or 2S,4R or 4S,5S)-2-Benzyl-5-[(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenylhexanoic Acids

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Title:Peptide Inhibitors of Aspartic Proteinases with Hydroxyethylene Isostere Replacement of Peptide Bond. I. Preparation of Four Diastereoisomeric (2R or 2S,4R or 4S,5S)-2-Benzyl-5-[(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenylhexanoic Acids
Creators:
Litera, Jaroslav
Buděšínský, Miloš
Urban, Ján
Souček, Milan
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 63, 2, pp. 231-244
Uncontrolled Keywords:Transition state analogues, γ-Lactones, 5-Amino-2-benzyl-4-hydroxy-6-phenylhexanoic acids, Hydroxyethylene isostere, Peptidomimetics, Diastereoisomers

Abstract

By two separate routes were prepared four diastereoisomers of (2<i>R </i>or 2<i>S</i>,5<i>R </i>or 5<i>S</i>)-3-benzyl-5-{(1<i>S</i>)- [(<i>tert</i>-butoxycarbonyl)amino]-2-phenylethyl}tetrahydrofuran-2-ones (<strong>11</strong>, <strong>12</strong>, <strong>17</strong> and <strong>18</strong>). Since the furanones were derived from (<i>S</i>)-phenylalanine, absolute configurations of all chiral carbon atoms could be deduced from their <sup>1</sup>H NMR spectra. The furanones were easily hydrolyzed to four (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-phenylbutanoic acids (<strong>20</strong>-<strong>23</strong>), hydroxyethylene isosteres of Phe-Phe peptide bond.

Title:Peptide Inhibitors of Aspartic Proteinases with Hydroxyethylene Isostere Replacement of Peptide Bond. I. Preparation of Four Diastereoisomeric (2R or 2S,4R or 4S,5S)-2-Benzyl-5-[(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenylhexanoic Acids
Creators:
Litera, Jaroslav
Buděšínský, Miloš
Urban, Ján
Souček, Milan
Uncontrolled Keywords:Transition state analogues, γ-Lactones, 5-Amino-2-benzyl-4-hydroxy-6-phenylhexanoic acids, Hydroxyethylene isostere, Peptidomimetics, Diastereoisomers
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:2
Page Range:pp. 231-244
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19980231UNSPECIFIED
ID Code:1291
Item Type:Article
Deposited On:06 Feb 2009 17:08
Last Modified:06 Feb 2009 16:08

Citation

Litera, Jaroslav; Buděšínský, Miloš; Urban, Ján; Souček, Milan (1998) Peptide Inhibitors of Aspartic Proteinases with Hydroxyethylene Isostere Replacement of Peptide Bond. I. Preparation of Four Diastereoisomeric (2R or 2S,4R or 4S,5S)-2-Benzyl-5-[(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenylhexanoic Acids. Collection of Czechoslovak Chemical Communications, 63 (2). pp. 231-244. ISSN 0010-0765

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