Skip to content

Research at St Andrews

Derivatisable cyanobactin analogues: a semisynthetic approach

Research output: Contribution to journalArticlepeer-review

Author(s)

Emilia Oueis, Catherine S Adamson, Greg Mann, Hannes Ludewig, Jim Naismith, Philip Redpath, Marie Migaud, Nicholas James Westwood, Jim Naismith

School/Research organisations

Abstract

Many natural cyclic peptides have potent and potentially useful biological activities. Their use as therapeutic starting points is often limited by the quantities available, the lack of known biological targets and the practical limits on diversification to fine-tune their properties. We report the use of enzymes from the cyanobactin family to heterocyclise and macrocyclise chemically synthesised substrates so as to allow larger-scale syntheses and better control over derivatisation. We have made cyclic peptides containing orthogonal reactive groups, azide or dehydroalanine, that allow chemical diversification, including the use of fluorescent labels that can help in target identification. We show that the enzymes are compatible and efficient with such unnatural substrates. The combination of chemical synthesis and enzymatic transformation could help renew interest in investigating natural cyclic peptides with biological activity, as well as their unnatural analogues, as therapeutics.
Close

Details

Original languageEnglish
Pages (from-to)2646-2650
JournalChemBioChem
Volume16
Issue number18
Early online date10 Nov 2015
DOIs
Publication statusPublished - 14 Dec 2015

    Research areas

  • Click chemistry, Cyclic peptides, Enzymatic reaction, Macrocyclisation, Patellamides

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

View graph of relations

Related by author

  1. Structure-activity relationships of the Human Immunodeficiency Virus type 1 maturation inhibitor PF-46396

    Murgatroyd, C., Pirrie, L., Tran, F., Smith, T. K., Westwood, N. J. & Adamson, C. S., Sep 2016, In: Journal of Virology. 90, 18, p. 8181-8197 17 p.

    Research output: Contribution to journalArticlepeer-review

  2. Valorisation of natural resources and the need for economic and sustainability assessment: the case of cocoa pod husk in Indonesia

    Picchioni, F., Warren, G. P., Lambert, S., Balcombe, K., Robinson, J. S., Srinivasan, C., D. Gomez, L., Faas, L., Westwood, N. J., Chatzifragkou, A., Charalampopoulos, D. & Shaw, L. J., 28 Oct 2020, In: Sustainability. 12, 21, 16 p., 8962.

    Research output: Contribution to journalArticlepeer-review

  3. Analysis of the product streams obtained on butanosolv pretreatment of draff

    Foltanyi, F., Hawkins, J. E., Panovic, I., Bird, E. J., Gloster, T., Lancefield, C. S. & Westwood, N. J., Oct 2020, In: Biomass and Bioenergy. 141, 105680.

    Research output: Contribution to journalArticlepeer-review

  4. Copper-mediated conversion of complex ethers to esters: enabling biopolymer depolymerisation under mild conditions

    Xiao, G., Montgomery, J., Lancefield, C. S., Panovic, I. & Westwood, N. J., 25 Sep 2020, In: Chemistry - A European Journal. 26, 54, p. 12397-12402 7 p.

    Research output: Contribution to journalArticlepeer-review

  5. Antiviral agent: discovery to resistance

    Adamson, C. S., 7 Apr 2020, In: Viruses. 12, 4, 3 p., 406.

    Research output: Contribution to journalEditorial

Related by journal

  1. SynBio-SynChem approaches to diversifying the pacidamycins through the exploitation of an observed Pictet-Spengler reaction

    Cartmell, C., Abou Fayad, A., Lynch, R., Sharma, S., Hauck, N., Gust, B. & Goss, R. J. M., 15 Jan 2021, In: ChemBioChem. 22, 6 p.

    Research output: Contribution to journalArticlepeer-review

  2. An engineered E. coli strain for direct in vivo fluorination

    Markakis, K., Lowe, P. T., Davison-Gates, L., O'Hagan, D., Rosser, S. J. & Elfick, A., 3 Mar 2020, In: ChemBioChem. Early View

    Research output: Contribution to journalArticlepeer-review

  3. Phenylalanine meta-hydroxylase: a single residue mediates mechanistic control of aromatic amino acid hydroxylation

    Gruschow, S., Sadler, J., Sharrat, P. & Goss, R. J. M., 3 Feb 2020, In: ChemBioChem. 21, 3, p. 417-422

    Research output: Contribution to journalArticlepeer-review

  4. Acetyl coenzyme A analogues as rationally designed inhibitors of citrate synthase

    Bello, D., Rubanu, M. G., Bandaranayaka, N., Götze, J. P., Bühl, M. & O'Hagan, D., 2 May 2019, In: ChemBioChem. 20, 9, p. 1174-1182

    Research output: Contribution to journalArticlepeer-review

  5. Enzymatic fluorination of biotin and tetrazine conjugates for pretargeting approaches to PET imaging

    Lowe, P. T., Dall'angelo, S., Devine, A., Zanda, M. & O'Hagan, D., 8 Aug 2018, In: ChemBioChem. In press

    Research output: Contribution to journalArticlepeer-review

ID: 229918479

Top