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Peptide β-Bend and 3 10 -Helix: from 3D-Structural Studies to Applications as Templates

  • Claudio Toniolo
  • Marco Crisma
  • Fernando Formaggio
  • Cristina Peggion
  • Quirinus Broxterman
  • Bernard Kaptein
Review Article

Abstract

The 3 10-helix is a relatively common secondary structure motif in peptides and proteins. Its building block is one of various types of β-bend conformation which comprises an N α-acylated dipeptide alkylamide system. A complete 3D-structural characterization of this ternary helix has been achieved, thus allowing its unambiguous discrimination from the closely related α-helix. Recent applications of rigidified peptide β-bends and 3 10-helices as templates for investigations in synthetic organic chemistry (macrocyclization, catalysis), host–guest chemistry (molecular recognition), and physical chemistry (donor–acceptor interaction) will be discussed.

Keywords

β-bend catalysis donor–acceptor interaction 3 10-helix host–guest chemistry macrocyclization peptide conformation Cα-tetrasubstituted α-amino acids 

Abbreviations

Ac

acetyl

Agl

Cα-allylglycine

Aib

α-aminoisobutyric acid (or Cα,α-dimethylglycine)

(αMe)Phg

Cα-methyl, Cα-phenylglycine

(αMe)Val

Cα-methyl valine

Api

4-amino-4-carboxypiperidine

ATANP

2-amino-3-[1-(1,4,7-triazacyclononane)] propanoic acid

Bin

2′,1′:1,2;1′′,2′′:3,4-dinaphthcyclohepta-1,3-diene-6-amino-6-carboxylic acid

Boc

tert-butyloxycarbonyl

Bpa

para-benzoyl-phenylalanine

Bz

benzoyl

DMSO

dimethylsulfoxide

ESR

electron spin resonance

Fmoc

fluoren-9-ylmethyloxycarbonyl

hhMag

homo-homo-Mag

hMag

homo-Mag

Mag

Cα-methyl, Cα-allylglycine

NHBzl

benzylamino

NHMe

methylamino

NHtBu

tert-butylamino

OMe

methoxy

OtBu

tert-butoxy

pBrBz

para-bromobenzoyl

Z

benzyloxycarbonyl

RCM

ring-closing metathesis

TEMPO

2,2,6,6-tetramethylpiperidinyl-1-oxy

TOAC

2,2,6,6-tetramethylpiperidine-1-oxy-4-amino-4-carboxylic acid

Tren

tris-(2-aminoethyl)amine

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Copyright information

© Springer 2005

Authors and Affiliations

  • Claudio Toniolo
    • 1
  • Marco Crisma
    • 1
  • Fernando Formaggio
    • 1
  • Cristina Peggion
    • 1
  • Quirinus Broxterman
    • 2
  • Bernard Kaptein
    • 2
  1. 1.Institute of Biomolecular Chemistry, CNR, Department of ChemistryUniversity of PadovaPadovaItaly
  2. 2.DSM Pharma ChemicalsAdvanced Synthesis and CatalysisGeleenThe Netherlands

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