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Literature DB >> 22568480

New preorganized γ-amino acids as foldamer building blocks.

Li Guo¹, Weicheng Zhang, Ilia A Guzei, Lara C Spencer, Samuel H Gellman.

Abstract

An asymmetric synthesis of two new diastereomeric γ-amino acids is described. Both molecules contain a cyclohexyl ring to limit conformational flexibility about the Cα-Cβ bond; they differ in having cis vs trans stereochemistry on the ring. Residues derived from the cis γ isomer are shown to support helical secondary structures in α/γ-peptide oligomers.

Entities: Chemical Species

Mesh：

Substances：

Year: 2012 PMID： 22568480 PMCID： PMC3445736 DOI： 10.1021/ol3008815

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

25 in total

1. Helix formation in alpha,gamma- and beta,gamma-hybrid peptides: theoretical insights into mimicry of alpha- and beta-peptides.

Authors: Carsten Baldauf; Robert Günther; Hans-Jörg Hofmann
Journal: J Org Chem Date: 2006-02-03 Impact factor: 4.354

2. Enforcing periodic secondary structures in hybrid peptides: a novel hybrid foldamer containing periodic gamma-turn motifs.

Authors: Pranjal K Baruah; N K Sreedevi; Rajesh Gonnade; Sapna Ravindranathan; Krishnan Damodaran; Hans-Jörg Hofmann; Gangadhar J Sanjayan
Journal: J Org Chem Date: 2007-01-19 Impact factor: 4.354

3. A beta/gamma motif to mimic alpha-helical turns in proteins.

Authors: Raheleh Rezaei Araghi; Christian Jäckel; Helmut Cölfen; Mario Salwiczek; Antje Völkel; Sara C Wagner; Sebastian Wieczorek; Carsten Baldauf; Beate Koksch
Journal: Chembiochem Date: 2010-02-15 Impact factor: 3.164

4. Structural and biological mimicry of protein surface recognition by alpha/beta-peptide foldamers.

Authors: W Seth Horne; Lisa M Johnson; Thomas J Ketas; Per Johan Klasse; Min Lu; John P Moore; Samuel H Gellman
Journal: Proc Natl Acad Sci U S A Date: 2009-08-17 Impact factor: 11.205

5. Polypeptide helices in hybrid peptide sequences.

Authors: Kuppanna Ananda; Prema G Vasudev; Anindita Sengupta; K Muruga Poopathi Raja; Narayanaswamy Shamala; Padmanabhan Balaram
Journal: J Am Chem Soc Date: 2005-11-30 Impact factor: 15.419

Review 6. The world of beta- and gamma-peptides comprised of homologated proteinogenic amino acids and other components.

Authors: Dieter Seebach; Albert K Beck; Daniel J Bierbaum
Journal: Chem Biodivers Date: 2004-08 Impact factor: 2.408

7. 12/10- and 11/13-mixed helices in alpha/gamma- and beta/gamma-hybrid peptides containing C-linked carbo-gamma-amino acids with alternating alpha- and beta-amino acids.

Authors: Gangavaram V M Sharma; Vivekanand B Jadhav; Kallaganti V S Ramakrishna; Pagadala Jayaprakash; Kongari Narsimulu; Velaparthi Subash; Ajit C Kunwar
Journal: J Am Chem Soc Date: 2006-11-15 Impact factor: 15.419

8. Environment-independent 14-helix formation in short beta-peptides: striking a balance between shape control and functional diversity.

Authors: Tami L Raguse; Jonathan R Lai; Samuel H Gellman
Journal: J Am Chem Soc Date: 2003-05-14 Impact factor: 15.419

New preorganized γ-amino acids as foldamer building blocks.

1. Helix formation in alpha,gamma- and beta,gamma-hybrid peptides: theoretical insights into mimicry of alpha- and beta-peptides.

2. Enforcing periodic secondary structures in hybrid peptides: a novel hybrid foldamer containing periodic gamma-turn motifs.

3. A beta/gamma motif to mimic alpha-helical turns in proteins.

4. Structural and biological mimicry of protein surface recognition by alpha/beta-peptide foldamers.

5. Polypeptide helices in hybrid peptide sequences.

Review 6. The world of beta- and gamma-peptides comprised of homologated proteinogenic amino acids and other components.

7. 12/10- and 11/13-mixed helices in alpha/gamma- and beta/gamma-hybrid peptides containing C-linked carbo-gamma-amino acids with alternating alpha- and beta-amino acids.

8. Environment-independent 14-helix formation in short beta-peptides: striking a balance between shape control and functional diversity.

9. Foldamers with heterogeneous backbones.

10. Expanding the peptide beta-turn in alphagamma hybrid sequences: 12 atom hydrogen bonded helical and hairpin turns.

1. Differential impact of β and γ residue preorganization on α/β/γ-peptide helix stability in water.

2. Evaluation of a cyclopentane-based γ-amino acid for the ability to promote α/γ-peptide secondary structure.