New templates for syntheses of ring-fused, C(10) beta-turn peptidomimetics leading to the first reported small-molecule mimic of neurotrophin-3. Academic Article

abstract

• beta-Turn peptidomimetics 1 were designed to mimic hot spots of neurotrophin-3 (NT-3) and others. Solid-phase syntheses of these were developed, though limitations were encountered with scale-up. Consequently, an alternative design with 2 was investigated. 1 and 2 favored distorted type I beta-turn conformations in solution. It was found that peptidomimetic 2b has NT-3-like neurotrophic activity in cell survival assays, selectively binds the NT-3 receptor TrkC, and induces the tyrosine phosphorylation of the TrkC receptor.

authors

• Burgess, Kevin

published proceedings

• J Med Chem

altmetric score

• 3

author list (cited authors)

• Pattarawarapan, M., Zaccaro, M. C., Saragovi, U. H., & Burgess, K.

citation count

• 25

complete list of authors

• Pattarawarapan, Mookda||Zaccaro, Maria Clara||Saragovi, Uri H||Burgess, Kevin

publication date

• September 2002

publisher

• American Chemical Society (ACS)  Publisher

published in

• Journal of Medicinal Chemistry  Journal

keywords

• 3T3 Cells
• Animals
• Cell Survival
• Circular Dichroism
• Flow Cytometry
• Mice
• Molecular Mimicry
• Neurotrophin 3
• Peptides
• Peptides, Cyclic
• Phosphorylation
• Protein Structure, Secondary
• Receptor, TrkA
• Receptor, Trkc
• Tyrosine

PubMed Central ID

• 12238916

Digital Object Identifier (DOI)

• 10.1021/jm0255421

start page

• 4387

end page

• 4390

volume

• 45

issue

• 20

URL

• http://dx.doi.org/10.1021/jm0255421