Cyclopropane Pipecolic Acids as Templates for Linear and Cyclic Peptidomimetics: Application in the Synthesis of an Arg‐Gly‐Asp (RGD)‐Containing Peptide as an α v β 3 Integrin Ligand
Abstract The synthesis and evaluation of substituted cyclopropane pipecolic acids (CPA) as conformationally restricted templates for linear and cyclic peptidomimetics is reported. A variety of differently substituted (poly)hydroxy‐ and amino‐2‐azabicyclo[4.1.0]heptane‐1‐carboxylic acids were prepare...
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| Published in | Chemistry : a European journal Vol. 20; no. 35; pp. 11187 - 11203 |
|---|---|
| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
25.08.2014
|
| Online Access | Get full text |
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| Abstract | Abstract
The synthesis and evaluation of substituted cyclopropane pipecolic acids (CPA) as conformationally restricted templates for linear and cyclic peptidomimetics is reported. A variety of differently substituted (poly)hydroxy‐ and amino‐2‐azabicyclo[4.1.0]heptane‐1‐carboxylic acids were prepared by means of the Pd‐catalyzed methoxycarbonylation of suitably functionalized lactam‐derived enol phosphates, followed by OH‐directed cyclopropanation. CPAs were successfully introduced into a linear peptide sequence to assess the
cis
/
trans
isomerism about the pipecolic acid peptide bond, and in a cyclic peptidomimetic that bore the Arg‐Gly‐Asp (RGD) sequence, which displayed nanomolar activity as antagonist of the α
v
β
3
integrin in M21 human melanoma cells. Thus, CPAs appear to be suitable for the generation of novel peptidomimetics for drug discovery. |
|---|---|
| AbstractList | Abstract
The synthesis and evaluation of substituted cyclopropane pipecolic acids (CPA) as conformationally restricted templates for linear and cyclic peptidomimetics is reported. A variety of differently substituted (poly)hydroxy‐ and amino‐2‐azabicyclo[4.1.0]heptane‐1‐carboxylic acids were prepared by means of the Pd‐catalyzed methoxycarbonylation of suitably functionalized lactam‐derived enol phosphates, followed by OH‐directed cyclopropanation. CPAs were successfully introduced into a linear peptide sequence to assess the
cis
/
trans
isomerism about the pipecolic acid peptide bond, and in a cyclic peptidomimetic that bore the Arg‐Gly‐Asp (RGD) sequence, which displayed nanomolar activity as antagonist of the α
v
β
3
integrin in M21 human melanoma cells. Thus, CPAs appear to be suitable for the generation of novel peptidomimetics for drug discovery. |
| Author | Sernissi, Lorenzo Petrović, Martina Trabocchi, Andrea Scarpi, Dina Occhiato, Ernesto G. Guarna, Antonio Bianchini, Francesca |
| Author_xml | – sequence: 1 givenname: Lorenzo surname: Sernissi fullname: Sernissi, Lorenzo – sequence: 2 givenname: Martina surname: Petrović fullname: Petrović, Martina – sequence: 3 givenname: Dina surname: Scarpi fullname: Scarpi, Dina – sequence: 4 givenname: Antonio surname: Guarna fullname: Guarna, Antonio – sequence: 5 givenname: Andrea surname: Trabocchi fullname: Trabocchi, Andrea – sequence: 6 givenname: Francesca surname: Bianchini fullname: Bianchini, Francesca – sequence: 7 givenname: Ernesto G. surname: Occhiato fullname: Occhiato, Ernesto G. |
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The synthesis and evaluation of substituted cyclopropane pipecolic acids (CPA) as conformationally restricted templates for linear and cyclic... |
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| Title | Cyclopropane Pipecolic Acids as Templates for Linear and Cyclic Peptidomimetics: Application in the Synthesis of an Arg‐Gly‐Asp (RGD)‐Containing Peptide as an α v β 3 Integrin Ligand |
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