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Title: A coupled chlorinase–fluorinase system with a high efficiency of trans -halogenation and a shared substrate tolerance

Abstract

SAM-dependent chlorinases exhibited tolerance to the modification at the C-2 position of the adenosine substrate and acted cooperatively with fluorinase for rapid trans -halogenation.

Authors:
ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [1]
  1. Metabolic Engineering Research Laboratory (MERL), Institute of Chemical & Engineering Sciences (ICES), Agency for Science, Technology and Research (A*STAR), Singapore 138669, Singapore
Publication Date:
Sponsoring Org.:
USDOE
OSTI Identifier:
1463186
Grant/Contract Number:  
SC0018420
Resource Type:
Publisher's Accepted Manuscript
Journal Name:
Chemical Communications
Additional Journal Information:
Journal Name: Chemical Communications Journal Volume: 54 Journal Issue: 68; Journal ID: ISSN 1359-7345
Publisher:
Royal Society of Chemistry (RSC)
Country of Publication:
United Kingdom
Language:
English

Citation Formats

Sun, H., Zhao, H., and Ang, E. L. A coupled chlorinase–fluorinase system with a high efficiency of trans -halogenation and a shared substrate tolerance. United Kingdom: N. p., 2018. Web. doi:10.1039/C8CC04436H.
Sun, H., Zhao, H., & Ang, E. L. A coupled chlorinase–fluorinase system with a high efficiency of trans -halogenation and a shared substrate tolerance. United Kingdom. doi:10.1039/C8CC04436H.
Sun, H., Zhao, H., and Ang, E. L. Mon . "A coupled chlorinase–fluorinase system with a high efficiency of trans -halogenation and a shared substrate tolerance". United Kingdom. doi:10.1039/C8CC04436H.
@article{osti_1463186,
title = {A coupled chlorinase–fluorinase system with a high efficiency of trans -halogenation and a shared substrate tolerance},
author = {Sun, H. and Zhao, H. and Ang, E. L.},
abstractNote = {SAM-dependent chlorinases exhibited tolerance to the modification at the C-2 position of the adenosine substrate and acted cooperatively with fluorinase for rapid trans -halogenation.},
doi = {10.1039/C8CC04436H},
journal = {Chemical Communications},
number = 68,
volume = 54,
place = {United Kingdom},
year = {2018},
month = {1}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
DOI: 10.1039/C8CC04436H

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Works referenced in this record:

Directed Evolution of a Fluorinase for Improved Fluorination Efficiency with a Non-native Substrate
journal, October 2016

  • Sun, Huihua; Yeo, Wan Lin; Lim, Yee Hwee
  • Angewandte Chemie International Edition, Vol. 55, Issue 46
  • DOI: 10.1002/anie.201606722

Fluorinase: a tool for the synthesis of 18 F-labeled sugars and nucleosides for PET
journal, August 2009

  • Onega, Mayca; Winkler, Margit; O’Hagan, David
  • Future Medicinal Chemistry, Vol. 1, Issue 5
  • DOI: 10.4155/fmc.09.74

An enzymatic route to 5-deoxy-5-[18F]fluoro-d-ribose, a [ 18 F]-fluorinated sugar for PET imaging
journal, January 2010

  • Onega, Mayca; Domarkas, Juozas; Deng, Hai
  • Chem. Commun., Vol. 46, Issue 1
  • DOI: 10.1039/B919364B

Fluoroacetate biosynthesis from the marine-derived bacterium Streptomyces xinghaiensis NRRL B-24674
journal, January 2014

  • Huang, Sheng; Ma, Long; Tong, Ming Him
  • Org. Biomol. Chem., Vol. 12, Issue 27
  • DOI: 10.1039/C4OB00970C

Discovery and characterization of a marine bacterial SAM-dependent chlorinase
journal, December 2007

  • Eustáquio, Alessandra S.; Pojer, Florence; Noel, Joseph P.
  • Nature Chemical Biology, Vol. 4, Issue 1
  • DOI: 10.1038/nchembio.2007.56

A Localized Tolerance in the Substrate Specificity of the Fluorinase Enzyme enables “Last-Step” 18 F Fluorination of a RGD Peptide under Ambient Aqueous Conditions
journal, July 2014

  • Thompson, Stephen; Zhang, Qingzhi; Onega, Mayca
  • Angewandte Chemie International Edition, Vol. 53, Issue 34
  • DOI: 10.1002/anie.201403345

Fluorinase-Coupled Base Swaps: Synthesis of [ 18 F]-5′-Deoxy-5′-fluorouridines
journal, December 2008

  • Winkler, Margit; Domarkas, Juozas; Schweiger, Lutz F.
  • Angewandte Chemie International Edition, Vol. 47, Issue 52
  • DOI: 10.1002/anie.200804040

Identification of Fluorinases from Streptomyces sp MA37, Norcardia brasiliensis , and Actinoplanes sp N902-109 by Genome Mining
journal, January 2014


Mechanism of Enzymatic Fluorination in Streptomyces c attleya
journal, November 2007

  • Zhu, Xiaofeng; Robinson, David A.; McEwan, Andrew R.
  • Journal of the American Chemical Society, Vol. 129, Issue 47
  • DOI: 10.1021/ja0731569

Biosynthesis of an organofluorine molecule
journal, March 2002

  • O'Hagan, David; Schaffrath, Christoph; Cobb, Steven L.
  • Nature, Vol. 416, Issue 6878
  • DOI: 10.1038/416279a

Enzymatic transhalogenation of dendritic RGD peptide constructs with the fluorinase
journal, January 2016

  • Thompson, Stephen; Fleming, Ian N.; O'Hagan, David
  • Organic & Biomolecular Chemistry, Vol. 14, Issue 11
  • DOI: 10.1039/C6OB00239K

Discovery of phosphonic acid natural products by mining the genomes of 10,000 actinomycetes
journal, August 2015

  • Ju, Kou-San; Gao, Jiangtao; Doroghazi, James R.
  • Proceedings of the National Academy of Sciences, Vol. 112, Issue 39
  • DOI: 10.1073/pnas.1500873112

Draft Genome Sequence of Streptomyces ahygroscopicus subsp. wuyiensis CK-15, Isolated from Soil in Fujian Province, China
journal, October 2015


A two-step fluorinase enzyme mediated 18 F labelling of an RGD peptide for positron emission tomography
journal, January 2015

  • Thompson, S.; Onega, M.; Ashworth, S.
  • Chemical Communications, Vol. 51, Issue 70
  • DOI: 10.1039/C5CC05013H

The Fluorinase fromStreptomyces cattleya Is Also a Chlorinase
journal, January 2006

  • Deng, Hai; Cobb, Steven L.; McEwan, Andrew R.
  • Angewandte Chemie International Edition, Vol. 45, Issue 5
  • DOI: 10.1002/anie.200503582

Isolation and characterisation of 5′-fluorodeoxyadenosine synthase, a fluorination enzyme from Streptomyces cattleya
journal, June 2003


antiSMASH 3.0—a comprehensive resource for the genome mining of biosynthetic gene clusters
journal, May 2015

  • Weber, Tilmann; Blin, Kai; Duddela, Srikanth
  • Nucleic Acids Research, Vol. 43, Issue W1
  • DOI: 10.1093/nar/gkv437

Specialised metabolites regulating antibiotic biosynthesis in Streptomyces spp.
journal, June 2016

  • Niu, Guoqing; Chater, Keith F.; Tian, Yuqing
  • FEMS Microbiology Reviews, Vol. 40, Issue 4
  • DOI: 10.1093/femsre/fuw012

γ-Butyrolactones: Streptomyces signalling molecules regulating antibiotic production and differentiation
journal, June 2006


Fluorinase mediated chemoenzymatic synthesis of [18F]-fluoroacetate
journal, January 2010

  • Li, Xiang-Guo; Domarkas, Juozas; O'Hagan, David
  • Chemical Communications, Vol. 46, Issue 41
  • DOI: 10.1039/c0cc02264k

A roadmap for natural product discovery based on large-scale genomics and metabolomics
journal, September 2014

  • Doroghazi, James R.; Albright, Jessica C.; Goering, Anthony W.
  • Nature Chemical Biology, Vol. 10, Issue 11
  • DOI: 10.1038/nchembio.1659

Clinical Application of Radiolabeled RGD Peptides for PET Imaging of Integrin α v β 3
journal, January 2016


Draft Genome Sequence of Streptomyces albulus Strain CCRC 11814, an  -Poly-L-Lysine-Producing Actinomycete
journal, August 2013