An Efficient synthesis of orthogonally protected<i>trans</i>- and<i>cis</i>-4-aminopipecolic acid

A stereodivergent strategy was devised to obtain enantiopure cis and trans 5-aminopipecolic acids (5-APAs) in suitably protected forms to be employed in peptide synthesis as conformationally constrained α- and δ-amino acids. The cis isomer was used as a δ-amino acid to construct a cyclic RGD-containing peptidomimetic, the ability of which to compete with biotinylated vitronectin for binding with the isolated αVβ3 integrin was measured (IC50 = 4.2 ± 0.9 nM). A complete 1H NMR and computational conformational analysis was performed to elucidate the reasons for the high affinity of this cyclic peptidomimetic in comparison with cilengitide.

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

hi@scite.ai

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

An Efficient synthesis of orthogonally protectedtrans- andcis-4-aminopipecolic acid

Cited by 5 publications

References 12 publications

An Efficient Synthesis of Orthogonally Protected trans‐ and cis‐4‐Aminopipecolic Acid.

An Efficient Synthesis of Orthogonally Protected trans‐ and cis‐4‐Aminopipecolic Acid.

Enantioselective Synthesis of cis and trans 4‐Aminopipecolic Acids as γ‐Amino Acids for the Construction of Cyclic RGD‐Containing Peptidomimetics Antagonists of α_Vβ₃ Integrin

Stereodivergent synthesis of 5-aminopipecolic acids and application in the preparation of a cyclic RGD peptidomimetic as a nanomolar α_Vβ₃ integrin ligand

Contact Info

Product

Resources

About

An Efficient synthesis of orthogonally protectedtrans- andcis-4-aminopipecolic acid

Cited by 5 publications

References 12 publications

An Efficient Synthesis of Orthogonally Protected trans‐ and cis‐4‐Aminopipecolic Acid.

An Efficient Synthesis of Orthogonally Protected trans‐ and cis‐4‐Aminopipecolic Acid.

Enantioselective Synthesis of cis and trans 4‐Aminopipecolic Acids as γ‐Amino Acids for the Construction of Cyclic RGD‐Containing Peptidomimetics Antagonists of αVβ3 Integrin

Stereodivergent synthesis of 5-aminopipecolic acids and application in the preparation of a cyclic RGD peptidomimetic as a nanomolar αVβ3 integrin ligand

Contact Info

Product

Resources

About

Enantioselective Synthesis of cis and trans 4‐Aminopipecolic Acids as γ‐Amino Acids for the Construction of Cyclic RGD‐Containing Peptidomimetics Antagonists of α_Vβ₃ Integrin

Stereodivergent synthesis of 5-aminopipecolic acids and application in the preparation of a cyclic RGD peptidomimetic as a nanomolar α_Vβ₃ integrin ligand