Literature DB >> 20055491

Functional characterization of the cyclomarin/cyclomarazine prenyltransferase CymD directs the biosynthesis of unnatural cyclic peptides.

Andrew W Schultz1, Chad A Lewis, Michael R Luzung, Phil S Baran, Bradley S Moore.   

Abstract

In vitro and in vivo characterization of the cyclomarin/cyclomarazine prenyltransferase CymD revealed its ability to prenylate tryptophan prior to incorporation into both cyclic peptides by the nonribosomal peptide synthetase CymA. This knowledge was utilized to bioengineer novel derivatives of these marine bacterial natural products by providing synthetic N-alkyl tryptophans to a prenyltransferase-deficient mutant of Salinispora arenicola CNS-205.

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Year:  2010        PMID： 20055491      PMCID： PMC2846197          DOI： 10.1021/np9006876

Source DB:  PubMed          Journal:  J Nat Prod        ISSN： 0163-3864            Impact factor:   4.050


  18 in total

1.  Dissection of malonyl-coenzyme A decarboxylation from polyketide formation in the reaction mechanism of a plant polyketide synthase.

Authors:  J M Jez; J L Ferrer; M E Bowman; R A Dixon; J P Noel
Journal:  Biochemistry       Date:  2000-02-08       Impact factor: 3.162

Review 2.  Total synthesis approaches to natural product derivatives based on the combination of chemical synthesis and metabolic engineering.

Authors:  Andreas Kirschning; Florian Taft; Tobias Knobloch
Journal:  Org Biomol Chem       Date:  2007-09-10       Impact factor: 3.876

3.  Reinvestigation of a cyclic dipeptide N-prenyltransferase reveals rearrangement of N-1 prenylated indole derivatives.

Authors:  Han-Li Ruan; Wen-Bing Yin; Ji-Zhou Wu; Shu-Ming Li
Journal:  Chembiochem       Date:  2008-05-05       Impact factor: 3.164

4.  Protein production by auto-induction in high density shaking cultures.

Authors:  F William Studier
Journal:  Protein Expr Purif       Date:  2005-05       Impact factor: 1.650

5.  A tyrosine O-prenyltransferase catalyses the first pathway-specific step in the biosynthesis of sirodesmin PL.

Authors:  Anika Kremer; Shu-Ming Li
Journal:  Microbiology (Reading)       Date:  2009-09-17       Impact factor: 2.777

6.  Biosynthesis and structures of cyclomarins and cyclomarazines, prenylated cyclic peptides of marine actinobacterial origin.

Authors:  Andrew W Schultz; Dong-Chan Oh; John R Carney; R Thomas Williamson; Daniel W Udwary; Paul R Jensen; Steven J Gould; William Fenical; Bradley S Moore
Journal:  J Am Chem Soc       Date:  2008-03-11       Impact factor: 15.419

7.  Lyngbyatoxin biosynthesis: sequence of biosynthetic gene cluster and identification of a novel aromatic prenyltransferase.

Authors:  Daniel J Edwards; William H Gerwick
Journal:  J Am Chem Soc       Date:  2004-09-22       Impact factor: 15.419

8.  A 7-dimethylallyltryptophan synthase from Aspergillus fumigatus: overproduction, purification and biochemical characterization.

Authors:  Anika Kremer; Lucia Westrich; Shu-Ming Li
Journal:  Microbiology       Date:  2007-10       Impact factor: 2.777

9.  The lyngbyatoxin biosynthetic assembly line: chain release by four-electron reduction of a dipeptidyl thioester to the corresponding alcohol.

Authors:  Jay A Read; Christopher T Walsh
Journal:  J Am Chem Soc       Date:  2007-11-29       Impact factor: 15.419

10.  Structural basis for the promiscuous biosynthetic prenylation of aromatic natural products.

Authors:  Tomohisa Kuzuyama; Joseph P Noel; Stéphane B Richard
Journal:  Nature       Date:  2005-06-16       Impact factor: 49.962
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  22 in total

1.  Identification and characterization of a bacterial cytochrome P450 monooxygenase catalyzing the 3-nitration of tyrosine in rufomycin biosynthesis.

Authors:  Hiroya Tomita; Yohei Katsuyama; Hiromichi Minami; Yasuo Ohnishi
Journal:  J Biol Chem       Date:  2017-08-03       Impact factor: 5.157

Review 2.  Structure and noncanonical chemistry of nonribosomal peptide biosynthetic machinery.

Authors:  Heather L Condurso; Steven D Bruner
Journal:  Nat Prod Rep       Date:  2012-06-25       Impact factor: 13.423

3.  N (1)-Fluoroalkyltryptophan Analogues: Synthesis and in vitro Study as Potential Substrates for Indoleamine 2,3-Dioxygenase.

Authors:  Jean Henrottin; Astrid Zervosen; Christian Lemaire; Frédéric Sapunaric; Sophie Laurent; Benoit Van den Eynde; Serge Goldman; Alain Plenevaux; André Luxen
Journal:  ACS Med Chem Lett       Date:  2015-01-25       Impact factor: 4.345

4.  Mechanistic studies on CymD: a tryptophan reverse N-prenyltransferase.

Authors:  Qi Qian; Andrew W Schultz; Bradley S Moore; Martin E Tanner
Journal:  Biochemistry       Date:  2012-09-19       Impact factor: 3.162

5.  A new group of aromatic prenyltransferases in fungi, catalyzing a 2,7-dihydroxynaphthalene 3-dimethylallyl-transferase reaction.

Authors:  Elisa Haug-Schifferdecker; Deniz Arican; Reinhard Brückner; Lutz Heide
Journal:  J Biol Chem       Date:  2010-03-29       Impact factor: 5.157

6.  Enzymatic basis of ribosomal peptide prenylation in cyanobacteria.

Authors:  John A McIntosh; Mohamed S Donia; Satish K Nair; Eric W Schmidt
Journal:  J Am Chem Soc       Date:  2011-08-04       Impact factor: 15.419

Review 7.  A sea of biosynthesis: marine natural products meet the molecular age.

Authors:  Amy L Lane; Bradley S Moore
Journal:  Nat Prod Rep       Date:  2010-12-17       Impact factor: 13.423

8.  Biochemical characterization of indole prenyltransferases: filling the last gap of prenylation positions by a 5-dimethylallyltryptophan synthase from Aspergillus clavatus.

Authors:  Xia Yu; Yan Liu; Xiulan Xie; Xiao-Dong Zheng; Shu-Ming Li
Journal:  J Biol Chem       Date:  2011-11-28       Impact factor: 5.157

Review 9.  The marine actinomycete genus Salinispora: a model organism for secondary metabolite discovery.

Authors:  Paul R Jensen; Bradley S Moore; William Fenical
Journal:  Nat Prod Rep       Date:  2015-05       Impact factor: 13.423

10.  Structural Basis of Tryptophan Reverse N-Prenylation Catalyzed by CymD.

Authors:  Benjamin W Roose; David W Christianson
Journal:  Biochemistry       Date:  2019-07-15       Impact factor: 3.162
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