Document 0513
 DOCN  M9590513
 TI    Stereoselective synthesis of Xaa psi[CH2CH(OH)]Yaa dipeptidomimetics and
       their inclusion in HIV-1 protease inhibitors.
 DT    9509
 AU    Chen HG; Tustin JM; Wuts PG; Sawyer TK; Smith CW; Upjohn Laboratories,
       Upjohn Company, Kalamazoo, Michigan, USA.
 SO    Int J Pept Protein Res. 1995 Jan;45(1):1-10. Unique Identifier :
       AIDSLINE MED/95293471
 AB    Two stereoselective syntheses of a new pseudodipeptide isostere, the
       right-hand hydroxyethylene dipeptidomimetic (Xaa psi[CH2CH(OH)]Yaa), are
       presented. In one method readily available amino acids are used as
       starting materials for Evans chiral aldol condensation chemistry. The
       second method relies on the synthesis of an anti-aldol product for the
       hydroxyethylene isostere via an E-selective ethyl hydrocinnamate
       enolization, and thus allows for the synthesis of isosteres having side
       chains other than those available from amino acids. Both methods are
       illustrated by the chiral synthesis of Boc-Phe psi[CH2CH(OH)]Phe. Two
       diastereomers, (S,S,R) and (S,R,R), are incorporated into an HIV-1
       protease inhibitor template which yields potent inhibitors of HIV-1
       protease when the pseudodipeptide isostere is Phe psi[CH(OH)CH2]Phe or
       Phe psi[CH(OH)CH(OH)]Phe. The resulting Phe psi[CH2CH(OH)]Phe-containing
       inhibitors possess modest potency.
 DE    Dipeptides/*CHEMISTRY  Drug Design  HIV Protease Inhibitors/*CHEMISTRY
       *HIV-1  Models, Chemical  Molecular Structure  Stereoisomers  JOURNAL
       ARTICLE

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