Poly-L-proline type II peptide mimics based on the 3-azabicyclo[3.1.0]hexane system

A. Mamai, R. Zhang, A. Natarajan, J. S. Madalengoitia

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

This paper describes conformational studies of proline-templated amino acids (PTAAs) based on the 3-azabicyclo[3.1.0]hexane system as well as conformational studies on short peptides composed of these PTAAs. NOE data, coupling constants, and molecular modeling are consistent with a flattened boat conformation for monomeric and oligomeric residues based on this bicyclic system. NMR studies on dimeric and trimeric oligomers are consistent with a populated poly-L-proline type II conformation in CDCl3 and D2O. Solution studies and molecular modeling predicts φ ∼ -70°, ψ ∼ 131°, χ1 ∼ -57°, and χ2 ∼ -158° for oligomeric residues.

Original languageEnglish (US)
Pages (from-to)455-460
Number of pages6
JournalJournal of Organic Chemistry
Volume66
Issue number2
DOIs
StatePublished - Jan 26 2001

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Molecular modeling
Proline
Conformations
Amino Acids
Peptides
Boats
Oligomers
Nuclear magnetic resonance
polyproline
3-azabicyclo(3.1.0)hexane

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Poly-L-proline type II peptide mimics based on the 3-azabicyclo[3.1.0]hexane system. / Mamai, A.; Zhang, R.; Natarajan, A.; Madalengoitia, J. S.

In: Journal of Organic Chemistry, Vol. 66, No. 2, 26.01.2001, p. 455-460.

Research output: Contribution to journalArticle

Mamai, A. ; Zhang, R. ; Natarajan, A. ; Madalengoitia, J. S. / Poly-L-proline type II peptide mimics based on the 3-azabicyclo[3.1.0]hexane system. In: Journal of Organic Chemistry. 2001 ; Vol. 66, No. 2. pp. 455-460.
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