Design and synthesis of oligoamide-based double α-helix mimetics

Oleg V. Kulikov, Sam Thompson, Hai Xu, Christopher D. Incarvito, Richard T W Scott, Ishu Saraogi, Laura Nevola, Andrew Hamilton

Research output: Contribution to journalArticle

Abstract

An extensive series of bis-oligobenzamides and bis-oligopyridylamides have been efficiently prepared and studied by X-ray analysis and computational methods. A modular synthesis led to double α-helix mimics bearing between two and ten branched side-chains. The inter-helix angle and distance can be tuned by varying the length and rigidity of the spacer, thereby reproducing the recognition domains of a range of super-secondary structures.

Original languageEnglish (US)
Pages (from-to)3433-3445
Number of pages13
JournalEuropean Journal of Organic Chemistry
Issue number17
DOIs
StatePublished - Jun 2013

Fingerprint

Bearings (structural)
X ray analysis
Computational methods
Rigidity
helices
synthesis
rigidity
spacers
x rays

Keywords

  • Amides
  • Helical structures
  • Hydrogen bonds
  • Peptidomimetics
  • Synthesis design

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry

Cite this

Kulikov, O. V., Thompson, S., Xu, H., Incarvito, C. D., Scott, R. T. W., Saraogi, I., ... Hamilton, A. (2013). Design and synthesis of oligoamide-based double α-helix mimetics. European Journal of Organic Chemistry, (17), 3433-3445. https://doi.org/10.1002/ejoc.201300363

Design and synthesis of oligoamide-based double α-helix mimetics. / Kulikov, Oleg V.; Thompson, Sam; Xu, Hai; Incarvito, Christopher D.; Scott, Richard T W; Saraogi, Ishu; Nevola, Laura; Hamilton, Andrew.

In: European Journal of Organic Chemistry, No. 17, 06.2013, p. 3433-3445.

Research output: Contribution to journalArticle

Kulikov, OV, Thompson, S, Xu, H, Incarvito, CD, Scott, RTW, Saraogi, I, Nevola, L & Hamilton, A 2013, 'Design and synthesis of oligoamide-based double α-helix mimetics', European Journal of Organic Chemistry, no. 17, pp. 3433-3445. https://doi.org/10.1002/ejoc.201300363
Kulikov OV, Thompson S, Xu H, Incarvito CD, Scott RTW, Saraogi I et al. Design and synthesis of oligoamide-based double α-helix mimetics. European Journal of Organic Chemistry. 2013 Jun;(17):3433-3445. https://doi.org/10.1002/ejoc.201300363
Kulikov, Oleg V. ; Thompson, Sam ; Xu, Hai ; Incarvito, Christopher D. ; Scott, Richard T W ; Saraogi, Ishu ; Nevola, Laura ; Hamilton, Andrew. / Design and synthesis of oligoamide-based double α-helix mimetics. In: European Journal of Organic Chemistry. 2013 ; No. 17. pp. 3433-3445.
@article{b5dd1f8cdef946a5828f54d10786477e,
title = "Design and synthesis of oligoamide-based double α-helix mimetics",
abstract = "An extensive series of bis-oligobenzamides and bis-oligopyridylamides have been efficiently prepared and studied by X-ray analysis and computational methods. A modular synthesis led to double α-helix mimics bearing between two and ten branched side-chains. The inter-helix angle and distance can be tuned by varying the length and rigidity of the spacer, thereby reproducing the recognition domains of a range of super-secondary structures.",
keywords = "Amides, Helical structures, Hydrogen bonds, Peptidomimetics, Synthesis design",
author = "Kulikov, {Oleg V.} and Sam Thompson and Hai Xu and Incarvito, {Christopher D.} and Scott, {Richard T W} and Ishu Saraogi and Laura Nevola and Andrew Hamilton",
year = "2013",
month = "6",
doi = "10.1002/ejoc.201300363",
language = "English (US)",
pages = "3433--3445",
journal = "Annalen der Pharmacie",
issn = "0075-4617",
publisher = "Wiley-VCH Verlag",
number = "17",

}

TY - JOUR

T1 - Design and synthesis of oligoamide-based double α-helix mimetics

AU - Kulikov, Oleg V.

AU - Thompson, Sam

AU - Xu, Hai

AU - Incarvito, Christopher D.

AU - Scott, Richard T W

AU - Saraogi, Ishu

AU - Nevola, Laura

AU - Hamilton, Andrew

PY - 2013/6

Y1 - 2013/6

N2 - An extensive series of bis-oligobenzamides and bis-oligopyridylamides have been efficiently prepared and studied by X-ray analysis and computational methods. A modular synthesis led to double α-helix mimics bearing between two and ten branched side-chains. The inter-helix angle and distance can be tuned by varying the length and rigidity of the spacer, thereby reproducing the recognition domains of a range of super-secondary structures.

AB - An extensive series of bis-oligobenzamides and bis-oligopyridylamides have been efficiently prepared and studied by X-ray analysis and computational methods. A modular synthesis led to double α-helix mimics bearing between two and ten branched side-chains. The inter-helix angle and distance can be tuned by varying the length and rigidity of the spacer, thereby reproducing the recognition domains of a range of super-secondary structures.

KW - Amides

KW - Helical structures

KW - Hydrogen bonds

KW - Peptidomimetics

KW - Synthesis design

UR - http://www.scopus.com/inward/record.url?scp=84878778905&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84878778905&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201300363

DO - 10.1002/ejoc.201300363

M3 - Article

AN - SCOPUS:84878778905

SP - 3433

EP - 3445

JO - Annalen der Pharmacie

JF - Annalen der Pharmacie

SN - 0075-4617

IS - 17

ER -