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

Journal of inclusion phenomena and macrocyclic chemistry volume 51, pages 121–136 (2005)Cite this 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.

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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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Authors and Affiliations

  1. Institute of Biomolecular Chemistry, CNR, Department of Chemistry, University of Padova, 35131, Padova, Italy

    Claudio Toniolo, Marco Crisma, Fernando Formaggio & Cristina Peggion

  2. DSM Pharma Chemicals, Advanced Synthesis and Catalysis, P.O. Box 18, 6160, MD, Geleen, The Netherlands

    Quirinus Broxterman & Bernard Kaptein

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  1. Claudio Toniolo
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  2. Marco Crisma
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  3. Fernando Formaggio
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Correspondence to Claudio Toniolo.

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Toniolo, C., Crisma, M., Formaggio, F. et al. Peptide β-Bend and 3 10 -Helix: from 3D-Structural Studies to Applications as Templates. J Incl Phenom Macrocycl Chem 51, 121–136 (2005). https://doi.org/10.1007/s10847-004-0912-z

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Keywords

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