Skip to content

Research at St Andrews

A systematic study of the solid state and solution phase conformational preferences of beta-peptides derived from transpentacin

Research output: Contribution to journalArticlepeer-review

Author(s)

Elin Abraham, Callum W. Bailey, Timothy D. W. Claridge, Stephen G. Davies, Kenneth B. Ling, Barbara Odell, Thomas L. Rees, Paul M. Roberts, Angela J. Russell, Andrew D. Smith, Lorna J. Smith, Helen R. Storr, Miles J. Sweet, Amber L. Thompson, James E. Thomson, George E. Tranter, David J. Watkin, Andrew David Smith

School/Research organisations

Abstract

The solid state and solution phase conformational preferences of a homologous series of beta-peptides derived from (S,S)-2-aminocyclopentanecarboxylic acid (transpentacin) have been investigated using a variety of spectroscopic and crystallographic techniques. These studies indicate that the hexamer and pentamer persist as a 12-helix in both the solid state and solution phase. Although the conformational traits of a 12-helix are exhibited by oligomers with as few as three residues in the solid state, in solution the trimer exists as an equilibrium of many alternative conformers whilst the tetramer has been shown to predominantly exist in either a 12-helix or a turn-type conformation. (C) 2010 Elsevier Ltd. All rights reserved.

Close

Details

Original languageEnglish
Pages (from-to)1797-1815
Number of pages19
JournalTetrahedron: Asymmetry
Volume21
Issue number13-14
DOIs
Publication statusPublished - 14 Jul 2010

    Research areas

  • 2-AMINOCYCLOPENTANECARBOXYLIC ACID-DERIVATIVES, HELICAL SECONDARY STRUCTURE, DE-NOVO DESIGN, ASYMMETRIC-SYNTHESIS, AQUEOUS-SOLUTION, FOLDAMERS, RESIDUES, (-)-(1R,2S)-CISPENTACIN, HEXAPEPTIDE, RESOLUTION

Discover related content
Find related publications, people, projects and more using interactive charts.

View graph of relations

Related by author

  1. Kinetic and Structure-Activity Studies of the Triazolium Ion- catalyzed Intramolecular Stetter Reaction

    Smith, A. D., Young, C. M. & O'Donoghue, A., 5 May 2021, (Accepted/In press) In: European Journal of Organic Chemistry.

    Research output: Contribution to journalArticlepeer-review

  2. Enantioselective synthesis of α-aryl-β2-amino-esters via cooperative isothiourea and Brønsted acid catalysis

    Zhao, F., Shu, C., Young, C. M., Carpenter-Warren, C., Slawin, A. M. Z. & Smith, A. D., 4 May 2021, In: Angewandte Chemie International Edition. Early View, 10 p.

    Research output: Contribution to journalArticlepeer-review

  3. Horeau amplification in the sequential acylative kinetic resolution of (±)-1,2-diols and (±)-1,3-diols in flow

    Brandolese, A., Greenhalgh, M. D., Qu, S., Desrues, T., Liu, X., Bressy, C. & Smith, A. D., 8 Mar 2021, In: Organic & Biomolecular Chemistry. Advance Article, 8 p.

    Research output: Contribution to journalArticlepeer-review

  4. α,β-Unsaturated acyl ammonium species as reactive intermediates in organocatalysis: an update

    Bitai, J., Westwood, M. & Smith, A. D., 1 Mar 2021, In: Organic & Biomolecular Chemistry. Advance Article, 19 p.

    Research output: Contribution to journalReview articlepeer-review

  5. Ultrarapid cerium(III)–NHC catalysts for high molar mass cyclic polylactide

    Kerr, R. W. F., Ewing, P., Raman, S. K., Smith, A. D., Williams, C. K. & Arnold, P. L., 15 Jan 2021, In: ACS Catalysis. 11, p. 1563-1569

    Research output: Contribution to journalArticlepeer-review

Related by journal

  1. Enantioselective N-heterocyclic carbene catalyzed formal [3+2] cycloaddition using α-aroyloxyaldehydes and oxaziridines

    Kerr, R. W. F., Greenhalgh, M. D., Slawin, A. M. Z., Arnold, P. L. & Smith, A. D., 15 Jan 2017, In: Tetrahedron: Asymmetry. 28, 1, p. 125-134

    Research output: Contribution to journalArticlepeer-review

  2. Enantioselective NHC-catalysed redox [4+2]-hetero-Diels-Alder reactions using α-aroyloxyaldehydes and unsaturated ketoesters

    Taylor, J. E., Davies, A. T., Douglas, J. J., Churchill, G. & Smith, A. D., 15 Feb 2017, In: Tetrahedron: Asymmetry. 28, 2, p. 355-366

    Research output: Contribution to journalArticlepeer-review

  3. Chiral fluoroacetic acid: synthesis of (R)- and (S)-[H-2(1)]-fluoroacetate in high enantiopurity

    Wadoux, R. D. P., Lin, X., Keddie, N. S. & O'Hagan, D., 30 Jun 2013, In: Tetrahedron: Asymmetry. 24, 12, p. 719-723 5 p.

    Research output: Contribution to journalArticlepeer-review

  4. Catalytic enantioselective Steglich rearrangements using chiral N-heterocyclic carbenes

    Campbell, C. D., Concellon, C. & Smith, A. D., 11 Apr 2011, In: Tetrahedron: Asymmetry. 22, 7, p. 797-811 15 p.

    Research output: Contribution to journalArticlepeer-review

ID: 5308227

Top