20032020

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2020

A Chemoenzymatic Approach to the Synthesis of Glycopeptide Antibiotic Analogues

Tailhades, J., Zhao, Y., Ho, Y. T. C., Greule, A., Ahmed, I., Schoppet, M., Kulkarni, K., Goode, R. J. A., Schittenhelm, R. B., De Voss, J. J. & Cryle, M. J., 15 Apr 2020, (Accepted/In press) In : Angewandte Chemie - International Edition. 6 p.

Research output: Contribution to journalArticleResearchpeer-review

1 Citation (Scopus)

Cellular and structural basis of synthesis of the unique intermediate dehydro-F420-0 in mycobacteria

Grinter, R., Ney, B., Brammananth, R., Barlow, C. K., Cordero, P. R. F., Gillett, D. L., Izoré, T., Cryle, M. J., Harold, L. K., Cook, G. M., Taiaroa, G., Williamson, D. A., Warden, A. C., Oakeshott, J. G., Taylor, M. C., Crellin, P. K., Jackson, C. J., Schittenhelm, R. B., Coppel, R. L. & Greening, C., Jun 2020, In : mSystems. 5, 3, 14 p., e00389-20.

Research output: Contribution to journalArticleResearchpeer-review

Open Access
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Exploring the Tetracyclization of Teicoplanin Precursor Peptides through Chemoenzymatic Synthesis

Zhao, Y., Goode, R. J. A., Schittenhelm, R. B., Tailhades, J. & Cryle, M. J., 7 Feb 2020, In : The Journal of Organic Chemistry. 85, 3, p. 1537-1547 11 p.

Research output: Contribution to journalArticleResearchpeer-review

2 Citations (Scopus)

Understanding the early stages of peptide formation during the biosynthesis of teicoplanin and related glycopeptide antibiotics

Kaniusaite, M., Tailhades, J., Kittilä, T., Fage, C. D., Goode, R. J. A., Schittenhelm, R. B. & Cryle, M. J., 2 May 2020, (Accepted/In press) In : FEBS Journal. 23 p.

Research output: Contribution to journalArticleResearchpeer-review

2019

Allelic association with ankylosing spondylitis fails to correlate with human leukocyte antigen B27 homodimer formation

Lim Kam Sian, T. C. C., Indumathy, S., Halim, H., Greule, A., Cryle, M. J., Bowness, P., Rossjohn, J., Gras, S., Purcell, A. W. & Schittenhelm, R. B., 27 Dec 2019, In : The Journal of Biological Chemistry. 294, 52, p. 20185-20195 11 p.

Research output: Contribution to journalArticleResearchpeer-review

A proof-reading mechanism for non-proteinogenic amino acid incorporation into glycopeptide antibiotics

Kaniusaite, M., Tailhades, J., Marschall, E. A., Goode, R. J. A., Schittenhelm, R. B. & Cryle, M. J., 29 Aug 2019, In : Chemical Science. 10, 41, p. 9466-9482 17 p.

Research output: Contribution to journalArticleResearchpeer-review

Open Access
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4 Citations (Scopus)

Drosophila melanogaster nonribosomal peptide synthetase Ebony encodes an atypical condensation domain

Izoré, T., Tailhades, J., Hansen, M. H., Kaczmarski, J. A., Jackson, C. J. & Cryle, M. J., 19 Feb 2019, In : Proceedings of the National Academy of Sciences of the United States of America. 116, 8, p. 2913-2918 6 p.

Research output: Contribution to journalArticleResearchpeer-review

3 Citations (Scopus)

Enzymatic Cascade to Evaluate the Tricyclization of Glycopeptide Antibiotic Precursor Peptides as a Prequel to Biosynthetic Redesign

Tailhades, J., Zhao, Y., Schoppet, M., Greule, A., Goode, R. J. A., Schittenhelm, R. B., De Voss, J. J. & Cryle, M. J., 1 Nov 2019, In : Organic Letters. 21, 21, p. 8635-8640 6 p.

Research output: Contribution to journalArticleResearchpeer-review

5 Citations (Scopus)

Kistamicin biosynthesis reveals the biosynthetic requirements for production of highly crosslinked glycopeptide antibiotics

Greule, A., Izoré, T., Iftime, D., Tailhades, J., Schoppet, M., Zhao, Y., Peschke, M., Ahmed, I., Kulik, A., Adamek, M., Goode, R. J. A., Schittenhelm, R. B., Kaczmarski, J. A., Jackson, C. J., Ziemert, N., Krenske, E. H., De Voss, J. J., Stegmann, E. & Cryle, M. J., 13 Jun 2019, In : Nature Communications. 10, 1, 15 p., 2613.

Research output: Contribution to journalArticleResearchpeer-review

Open Access
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11 Citations (Scopus)

The biosynthetic implications of late-stage condensation domain selectivity during glycopeptide antibiotic biosynthesis

Schoppet, M., Peschke, M., Kirchberg, A., Wiebach, V., Süssmuth, R. D., Stegmann, E. & Cryle, M. J., 1 Jan 2019, In : Chemical Science. 10, 1, p. 118-133 16 p.

Research output: Contribution to journalArticleResearchpeer-review

Open Access
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7 Citations (Scopus)

The Diiron Monooxygenase CmlA from Chloramphenicol Biosynthesis Allows Reconstitution of β-Hydroxylation during Glycopeptide Antibiotic Biosynthesis

Kaniusaite, M., Goode, R. J. A., Schittenhelm, R. B., Makris, T. M. & Cryle, M. J., 20 Dec 2019, In : ACS Chemical Biology. 14, 12, 10 p.

Research output: Contribution to journalArticleResearchpeer-review

Two uptake hydrogenases differentially interact with the aerobic respiratory chain during mycobacterial growth and persistence

Cordero, P. R. F., Grinter, R., Hards, K., Cryle, M. J., Warr, C. G., Cook, G. M. & Greening, C., 17 Oct 2019, In : The Journal of Biological Chemistry. 294, 50, p. 18980-18991 12 p.

Research output: Contribution to journalArticleResearchpeer-review

5 Citations (Scopus)
2018

An enhanced chemoenzymatic method for loading substrates onto carrier protein domains

Kittilä, T. & Cryle, M. J., 1 Jan 2018, In : Biochemistry and Cell Biology. 96, 3, p. 372-379 8 p.

Research output: Contribution to journalArticleResearchpeer-review

3 Citations (Scopus)

A route to diastereomerically pure phenylglycine thioester peptides: Crucial intermediates for investigating glycopeptide antibiotic biosynthesis

Tailhades, J., Schoppet, M., Greule, A., Peschke, M., Brieke, C. & Cryle, M. J., 9 Feb 2018, In : Chemical Communications. 54, 17, p. 2146-2149 4 p.

Research output: Contribution to journalArticleResearchpeer-review

Open Access
File
14 Citations (Scopus)

Investigating Cytochrome P450 specificity during glycopeptide antibiotic biosynthesis through a homologue hybridization approach

Brieke, C., Tarnawski, M., Greule, A. & Cryle, M. J., 1 Aug 2018, In : Journal of Inorganic Biochemistry. 185, p. 43-51 9 p.

Research output: Contribution to journalArticleResearchpeer-review

3 Citations (Scopus)

Precursor Manipulation in Glycopeptide Antibiotic Biosynthesis: Are β-Amino Acids Compatible with the Oxidative Cyclization Cascade?

Schoppet, M., Tailhades, J., Kulkarni, K. & Cryle, M. J., 6 Jul 2018, In : The Journal of Organic Chemistry. 83, 13, p. 7206-7214 9 p.

Research output: Contribution to journalArticleResearchpeer-review

5 Citations (Scopus)

The Thioesterase Domain in Glycopeptide Antibiotic Biosynthesis Is Selective for Cross-Linked Aglycones

Peschke, M., Brieke, C., Heimes, M. & Cryle, M. J., 19 Jan 2018, In : ACS Chemical Biology. 13, 1, p. 110-120 11 p.

Research output: Contribution to journalArticleResearchpeer-review

Open Access
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5 Citations (Scopus)
2017

Chlorinated Glycopeptide Antibiotic Peptide Precursors Improve Cytochrome P450-Catalyzed Cyclization Cascade Efficiency

Peschke, M., Brieke, C., Goode, R. J. A., Schittenhelm, R. B. & Cryle, M. J., 7 Mar 2017, In : Biochemistry. 56, 9, p. 1239-1247 9 p.

Research output: Contribution to journalArticleResearchpeer-review

17 Citations (Scopus)

Halogenation of glycopeptide antibiotics occurs at the amino acid level during non-ribosomal peptide synthesis

Kittilä, T., Kittel, C., Tailhades, J., Butz, D., Schoppet, M., Büttner, A., Goode, R. J. A., Schittenhelm, R. B., Van Pee, K. H., Süssmuth, R. D., Wohlleben, W., Cryle, M. J. & Stegmann, E., 13 Jul 2017, In : Chemical Science. 8, 9, p. 5992-6004 13 p.

Research output: Contribution to journalArticleResearchpeer-review

Open Access
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22 Citations (Scopus)

P450 monooxygenase ComJ catalyses side chain phenolic cross-coupling during complestatin biosynthesis

Mollo, A., von Krusenstiern, A. N., Bulos, J. A., Ulrich, V., Åkerfeldt, K. S., Cryle, M. J. & Charkoudian, L. K., 12 Jul 2017, In : RSC Advances. 7, 56, p. 35376-35384 9 p.

Research output: Contribution to journalArticleResearchpeer-review

Open Access
File
6 Citations (Scopus)

SNaPe: A versatile method to generate multiplexed protein fusions using synthetic linker peptides for in vitro applications

Ulrich, V. & Cryle, M. J., Jan 2017, In : Journal of Peptide Science. 23, 1, p. 16-27 12 p.

Research output: Contribution to journalArticleResearchpeer-review

1 Citation (Scopus)

Uncovering protein–protein interactions through a team-based undergraduate biochemistry course

Cookmeyer, D. L., Winesett, E. S., Kokona, B., Huff, A. R., Aliev, S., Bloch, N. B., Bulos, J. A., Evans, I. L., Fagre, C. R., Godbe, K. N., Khromava, M., Konstantinovsky, D. M., Lafrance, A. E., Lamacki, A. J., Parry, R. C., Quinn, J. M., Thurston, A. M., Tsai, K. J. S., Mollo, A., Cryle, M. J. & 2 others, Fairman, R. & Charkoudian, L. K., 1 Nov 2017, In : PLoS Biology. 15, 11, 13 p., e2003145.

Research output: Contribution to journalArticleResearchpeer-review

Open Access
File
8 Citations (Scopus)
2016

Biochemical and structural characterisation of the second oxidative crosslinking step during the biosynthesis of the glycopeptide antibiotic A47934

Ulrich, V., Brieke, C. & Cryle, M. J., 27 Dec 2016, In : Beilstein Journal of Organic Chemistry. 12, p. 2849-2864 16 p.

Research output: Contribution to journalArticleResearchpeer-review

Open Access
File
9 Citations (Scopus)

Catalytic promiscuity of glycopeptide N-methyltransferases enables bio-orthogonal labelling of biosynthetic intermediates

Brieke, C., Yim, G., Peschke, M., Wright, G. D. & Cryle, M. J., Nov 2016, In : Chemical Communications. 52, 94, p. 13679-13682 4 p.

Research output: Contribution to journalArticleOtherpeer-review

3 Citations (Scopus)

Design and synthesis of peptide inhibitor conjugates as probes of the Cytochrome P450s from glycopeptide antibiotic biosynthesis

Brieke, C., Maier, T., Schröter, M. & Cryle, M. J., 2016, In : MedChemComm. 7, 1, p. 132-140 9 p.

Research output: Contribution to journalArticleResearchpeer-review

F-O-G ring formation in glycopeptide antibiotic biosynthesis is catalysed by OxyE

Peschke, M., Brieke, C. & Cryle, M. J., 18 Oct 2016, In : Scientific Reports. 6, 9 p., 35584.

Research output: Contribution to journalArticleResearchpeer-review

Open Access
File
22 Citations (Scopus)

More than just recruitment: The X-domain influences catalysis of the first phenolic coupling reaction in A47934 biosynthesis by Cytochrome P450 StaH

Ulrich, V., Peschke, M., Brieke, C. & Cryle, M. J., Oct 2016, In : Molecular BioSystems. 12, 10, p. 2992-3004 13 p.

Research output: Contribution to journalArticleResearchpeer-review

16 Citations (Scopus)

Online pyrophosphate assay for analyzing adenylation domains of nonribosomal peptide synthetases

Kittila, T., Schoppet, M. & Cryle, M. J., 1 Apr 2016, In : ChemBioChem. 17, 7, p. 576-584 9 p.

Research output: Contribution to journalArticleResearchpeer-review

20 Citations (Scopus)

Probing the selectivity of β-hydroxylation reactions in non-ribosomal peptide synthesis using analytical ultracentrifugation

Kokona, B., Winesett, E. S., von Krusenstiern, A. N., Cryle, M. J., Fairman, R. & Charkoudian, L. K., 15 Feb 2016, In : Analytical Biochemistry. 495, p. 42-51 10 p.

Research output: Contribution to journalArticleResearchpeer-review

8 Citations (Scopus)

Regulation of the P450 oxygenation cascade involved in glycopeptide antibiotic biosynthesis

Peschke, M., Haslinger, K., Brieke, C., Reinstein, J. & Cryle, M. J., 23 May 2016, In : Journal of the American Chemical Society. 138, 21, p. 6746-6753 8 p.

Research output: Contribution to journalArticleResearchpeer-review

33 Citations (Scopus)

Structure of OxyAtei : Completing our picture of the glycopeptide antibiotic producing Cytochrome P450 cascade

Haslinger, K. & Cryle, M. J., Feb 2016, In : FEBS Letters. 590, 4, p. 571-581 11 p.

Research output: Contribution to journalArticleResearchpeer-review

11 Citations (Scopus)
2015

Rapid access to glycopeptide antibiotic precursor peptides coupled with cytochrome P450-mediated catalysis: Towards a biomimetic synthesis of glycopeptide antibiotics

Brieke, C., Kratzig, V., Haslinger, K., Winkler, A. & Cryle, M. J., 21 Feb 2015, In : Organic and Biomolecular Chemistry. 13, 7, p. 2012-2021 10 p.

Research output: Contribution to journalArticleResearchpeer-review

26 Citations (Scopus)

Sequential in Vitro Cyclization by Cytochrome P450 Enzymes of Glycopeptide Antibiotic Precursors Bearing the X-Domain from Nonribosomal Peptide Biosynthesis

Brieke, C., Peschke, M., Haslinger, K. & Cryle, M. J., 21 Dec 2015, In : Angewandte Chemie - International Edition. 54, 52, p. 15715-15719 5 p.

Research output: Contribution to journalArticleResearchpeer-review

37 Citations (Scopus)

Structure of the terminal PCP domain of the non-ribosomal peptide synthetase in teicoplanin biosynthesis

Haslinger, K., Redfield, C. & Cryle, M. J., 1 Apr 2015, In : Proteins: Structure, Function, and Bioinformatics. 83, 4, p. 711-721 11 p.

Research output: Contribution to journalArticleResearchpeer-review

19 Citations (Scopus)

The crystal structure of the versatile cytochrome P450 enzyme CYP109B1 from Bacillus subtilis

Zhang, A., Zhang, T., Hall, E. A., Hutchinson, S., Cryle, M. J., Wong, L. L., Zhou, W. & Bell, S. G., 1 Mar 2015, In : Molecular BioSystems. 11, 3, p. 869-881 13 p.

Research output: Contribution to journalArticleResearchpeer-review

11 Citations (Scopus)

X-domain of peptide synthetases recruits oxygenases crucial for glycopeptide biosynthesis

Haslinger, K., Peschke, M., Brieke, C., Maximowitsch, E. & Cryle, M. J., 7 May 2015, In : Nature. 521, 7550, p. 105-109 5 p.

Research output: Contribution to journalArticleResearchpeer-review

86 Citations (Scopus)
2014

A facile Fmoc solid phase synthesis strategy to access epimerization-prone biosynthetic intermediates of glycopeptide antibiotics

Brieke, C. & Cryle, M. J., 14 Apr 2014, In : Organic Letters. 16, 9, p. 2454-2457 4 p.

Research output: Contribution to journalArticleResearchpeer-review

38 Citations (Scopus)

Cytochrome P450 OxyBtei catalyzes the first phenolic coupling step in teicoplanin biosynthesis

Haslinger, K., Maximowitsch, E., Brieke, C., Koch, A. & Cryle, M. J., 15 Dec 2014, In : ChemBioChem. 15, 18, p. 2719-2728 10 p.

Research output: Contribution to journalArticleResearchpeer-review

34 Citations (Scopus)

The structure of a transient complex of a nonribosomal peptide synthetase and a cytochrome P450 monooxygenase

Haslinger, K., Brieke, C., Uhlmann, S., Sieverling, L., Sussmuth, R. D. & Cryle, M. J., 4 Aug 2014, In : Angewandte Chemie - International Edition. 53, 32, p. 8518-8522 5 p.

Research output: Contribution to journalArticleResearchpeer-review

45 Citations (Scopus)
2013

Cytochrome p450sky interacts directly with the nonribosomal peptide synthetase to generate three amino acid precursors in skyllamycin biosynthesis

Uhlmann, S., Sussmuth, R. D. & Cryle, M., 2013, In : ACS Chemical Biology. 8, 11, p. 2586 - 2596 11 p.

Research output: Contribution to journalArticleResearchpeer-review

43 Citations (Scopus)

Inner-shell multiple ionization of polyatomic molecules with an intense x-ray free-electron laser studied by coincident ion momentum imaging

Erk, B., Rolles, D., Foucar, L., Rudek, B., Epp, S. W., Cryle, M. J., Bostedt, C., Schorb, S., Bozek, J. D., Rouzee, A., Hundertmark, A., Marchenko, T., Simon, M., Filsinger, F., Christensen, L., De, S., Trippel, S., Kupper, J., Stapelfeldt, H., Wada, S. & 8 others, Ueda, K., Swiggers, M., Messerschmidt, M., Schroter, C. D., Moshammer, R., Schlichting, I., Ullrich, J. & Rudenko, A., 2013, In : Journal of Physics B: Atomic, Molecular and Optical Physics. 46, Article #164031, p. 1 - 12 12 p.

Research output: Contribution to journalArticleResearchpeer-review

20 Citations (Scopus)

Ultrafast charge rearrangement and nuclear dynamics upon inner-shell multiple ionization of small polyatomic molecules

Erk, B., Rolles, D., Foucar, L., Rudek, B., Epp, S. W., Cryle, M. J., Bostedt, C., Schorb, S., Bozek, J. D., Rouzee, A., Hundertmark, A., Marchenko, T., Simon, M., Filsinger, F., Christensen, L., De, S., Trippel, S., Kupper, J., Stapelfeldt, H., Wada, S. & 8 others, Ueda, K., Swiggers, M., Messerschmidt, M., Schroter, C. D., Moshammer, R., Schlichting, I., Ullrich, J. & Rudenko, A., 2013, In : Physical Review Letters. 110, 5, p. 1 - 5 5 p.

Research output: Contribution to journalArticleResearchpeer-review

70 Citations (Scopus)
2012

Coulomb explosion imaging of small organic molecules at LCLS

Erk, B., Rudenko, A., Rolles, D., Rudek, B., Foucar, L., Epp, S. W., Cryle, M., Schlichting, I., Bostedt, C., Schorb, S., Bozek, J. D., Rouzee, A., Hundertmark, A., Marchenko, T., Simon, M., Filsinger, F., Christensen, L., Ganesh, S., Trippel, S., Wada, S. & 3 others, Ueda, K., Dieter Schroeter, C. & Ullrich, J., 2012, In : Journal of Physics: Conference Series. 388, PART 2, 022108.

Research output: Contribution to journalArticleResearchpeer-review

Open Access

Enzyme-substrate complementarity governs access to a cationic reaction manifold in the P450(BM3)-catalysed oxidation of cyclopropyl fatty acids

Cryle, M. J., Hayes, P. Y. & De Voss, J. J., 2012, In : Chemistry - A European Journal. 18, 50, p. 15994 - 15999 6 p.

Research output: Contribution to journalArticleResearchpeer-review

8 Citations (Scopus)

Femtosecond free-electron laser x-ray diffraction data sets for algorithm development

Kassemeyer, S., Steinbrener, J., Lomb, L., Hartmann, E., Aquila, A. L., Barty, A., Martin, A. V., Hampton, C. Y., Bajt, S., Barthelmess, M., Barends, T. R. M., Bostedt, C., Bott, M., Bozek, J. D., Coppola, N., Cryle, M. J., DePonte, D. P., Doak, R. B., Epp, S. W., Erk, B. & 42 others, Fleckenstein, H., Foucar, L., Graafsma, H., Gumprecht, L., Hartmann, A., Hartmann, R., Hauser, G., Hirsemann, H., Homke, A., Holl, P., Jonsson, O., Kimmel, N., Krasniqi, F., Liang, M., Maia, F. R. N. C., Marchesini, S., Nass, K., Reich, C., Rolles, D., Rudek, B., Rudenko, A., Schmidt, C., Schulz, J., Shoeman, R. L., Sierra, R. G., Soltau, H., Spence, J. C. H., Starodub, D., Stellato, F., Stern, S., Stier, G., Svenda, M., Weidenspointner, G., Weierstall, U., White, T. A., Wunderer, C., Frank, M., Chapman, H. N., Ullrich, J., Struder, L., Bogan, M. J. & Schlichting, I., 2012, In : Optics Express. 20, 4, p. 4149 - 4158 10 p.

Research output: Contribution to journalArticleResearchpeer-review

Open Access
54 Citations (Scopus)
2011

Carrier protein substrates in cytochrome P450-catalysed oxidation

Cryle, M. J., 2011, In : Metallomics. 3, 4, p. 323 - 326 4 p.

Research output: Contribution to journalArticleResearchpeer-review

21 Citations (Scopus)

Structural characterization of CYP165D3, a cytochrome P450 involved in phenolic coupling in teicoplanin biosynthesis

Cryle, M. J., Staaden, J. & Schlichting, I., 2011, In : Archives of Biochemistry and Biophysics. 507, 1, p. 163 - 173 11 p.

Research output: Contribution to journalArticleResearchpeer-review

23 Citations (Scopus)
2010

Selectivity in a barren landscape: the P450(BioI)-ACP complex

Cryle, M. J., 2010, In : Biochemical Society Transactions. 38, 4, p. 934 - 939 6 p.

Research output: Contribution to journalArticleResearchpeer-review

13 Citations (Scopus)

Structural and biochemical characterization of the cytochrome P450 CypX (CYP134A1) from Bacillus subtilis: a cyclo-L-leucyl-L-leucyl dipeptide oxidase

Cryle, M. J., Bell, S. G. & Schlichting, I., 2010, In : Biochemistry. 49, 34, p. 7282 - 7296 15 p.

Research output: Contribution to journalArticleResearchpeer-review

50 Citations (Scopus)

Structural characterization of OxyD, a cytochrome P450 involved in beta-hydroxytyrosine formation in vancomycin biosynthesis

Cryle, M. J., Meinhart, A. & Schlichting, I., 2010, In : The Journal of Biological Chemistry. 285, 32, p. 24562 - 24574 13 p.

Research output: Contribution to journalArticleResearchpeer-review

43 Citations (Scopus)