Design and Enantioselective Synthesis of a Peptidomimetic of the Turn in the Helix-Turn-Helix DNA-Binding Protein Motif

Journal of Organic Chemistry

Volumn 62, Issue 24, 1997, Pages 8387-8393

  Travins, Jeremy M ^a   Etzkorn, Felicia A ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000452473     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971077h     Document Type: Article

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33. 25 However, in our sterically congested target, the reaction of benzyl 2-(Cbz)amino-2-(dimethoxyphosphoryl)acetylglycinate with 6 gave a very poor yield in the second Horner-Wittig reaction. Inverting the order by reacting the dipeptide phosphonate in the first step and 3 in the second step did not improve the yield. We concluded that stepwise synthesis of the tripeptide backbone was necessary and suitable for cassette synthesis with amino acids other than Gly.
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