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Literature DB >> 20518540

Design, synthesis, and structural analysis of D,L-mixed polypyrrolinones. 1. From nonpeptide peptidomimetics to nanotubes.

Amos B Smith¹, Wenyong Wang, Adam K Charnley, Patrick J Carroll, Craig S Kenesky, Ralph Hirschmann.

Abstract

To expand the potential conformational space available to the polypyrroline structural motif, an open chain, D,L-alternating hexapyrrolinone was designed and synthesized. Structural studies, including solution NMR and X-ray crystallographic analysis, revealed that the hexapyrrolinone adopts a turn conformation both in solution and in the solid state, with aggregation in solution and a nanotube-like quaternary structure in the crystal.

Entities: Chemical Disease Gene Species

Mesh：

Substances：
Polymers
Pyrrolidinones

Year: 2010 PMID： 20518540 PMCID： PMC2892756 DOI： 10.1021/ol101007n

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

16 in total

Review 1. Designed molecules that fold to mimic protein secondary structures.

Authors: K D Stigers; M J Soth; J S Nowick
Journal: Curr Opin Chem Biol Date: 1999-12 Impact factor: 8.822

Review 2. A field guide to foldamers.

Authors: D J Hill; M J Mio; R B Prince; T S Hughes; J S Moore
Journal: Chem Rev Date: 2001-12 Impact factor: 60.622

3. Self-assembling organic nanotubes based on a cyclic peptide architecture.

Authors: M R Ghadiri; J R Granja; R A Milligan; D E McRee; N Khazanovich
Journal: Nature Date: 1993-11-25 Impact factor: 49.962

4. Molecular modeling, synthesis, and structures of N-methylated 3,5-linked pyrrolin-4-ones toward the creation of a privileged nonpeptide scaffold.

Authors: A B Smith; D A Favor; P A Sprengeler; M C Guzman; P J Carroll; G T Furst; R Hirschmann
Journal: Bioorg Med Chem Date: 1999-01 Impact factor: 3.641

5. Regularly alternating L,D-peptides. III. Hexacyclic peptides from valine or phenylalanine.

Authors: V Pavone; E Benedetti; B Di Blasio; A Lombardi; C Pedone; L Tomasich; G P Lorenzi
Journal: Biopolymers Date: 1989-01 Impact factor: 2.505

6. Design, synthesis, and biological evaluation of monopyrrolinone-based HIV-1 protease inhibitors.

Authors: Amos B Smith; Louis-David Cantin; Alexander Pasternak; Lisa Guise-Zawacki; Wenquin Yao; Adam K Charnley; Joseph Barbosa; Paul A Sprengeler; Ralph Hirschmann; Sanjeev Munshi; David B Olsen; William A Schleif; Lawrence C Kuo
Journal: J Med Chem Date: 2003-05-08 Impact factor: 7.446

Design, synthesis, and structural analysis of D,L-mixed polypyrrolinones. 1. From nonpeptide peptidomimetics to nanotubes.

Review 1. Designed molecules that fold to mimic protein secondary structures.

Review 2. A field guide to foldamers.

3. Self-assembling organic nanotubes based on a cyclic peptide architecture.

4. Molecular modeling, synthesis, and structures of N-methylated 3,5-linked pyrrolin-4-ones toward the creation of a privileged nonpeptide scaffold.

5. Regularly alternating L,D-peptides. III. Hexacyclic peptides from valine or phenylalanine.

6. Design, synthesis, and biological evaluation of monopyrrolinone-based HIV-1 protease inhibitors.

7. Crystal structure of the 1:1 mixture of cyclic (L-Ala-L-Pro-L-Phe-L-Pro) and cyclic (L-Ala-L-Pro-D-Phe-L-Pro).

8. Foldamers with heterogeneous backbones.

9. Somatostatin analogs which define the role of the lysine-9 amino group.

10. Design and synthesis of nonpeptide peptidomimetic inhibitors of renin.

1. Pyrrolinone-based peptidomimetics. "Let the enzyme or receptor be the judge".