Literature DB >> 18512922

Engineered biosynthesis of antiprotealide and other unnatural salinosporamide proteasome inhibitors.

Ryan P McGlinchey1, Markus Nett, Alessandra S Eustáquio, Ratnakar N Asolkar, William Fenical, Bradley S Moore.   

Abstract

A new shunt in the phenylalanine biosynthetic pathway to the nonproteinogenic amino acid L-3-cyclohex-2'-enylalanine was exploited in the marine bacterium Salinispora tropica by mutagenesis to allow for the genetic engineering of unnatural derivatives of the potent proteasome inhibitor salinosporamide A (2) such as antiprotealide (1).

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Year:  2008        PMID： 18512922      PMCID： PMC2814216          DOI： 10.1021/ja8029398

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  19 in total

1.  The specificity-conferring code of adenylation domains in nonribosomal peptide synthetases.

Authors:  T Stachelhaus; H D Mootz; M A Marahiel
Journal:  Chem Biol       Date:  1999-08

2.  The gene cluster for chloramphenicol biosynthesis in Streptomyces venezuelae ISP5230 includes novel shikimate pathway homologues and a monomodular non-ribosomal peptide synthetase gene.

Authors:  J He; N Magarvey; M Piraee; L C Vining
Journal:  Microbiology       Date:  2001-10       Impact factor: 2.777

3.  Salinosporamide A: a highly cytotoxic proteasome inhibitor from a novel microbial source, a marine bacterium of the new genus salinospora.

Authors:  Robert H Feling; Greg O Buchanan; Tracy J Mincer; Christopher A Kauffman; Paul R Jensen; William Fenical
Journal:  Angew Chem Int Ed Engl       Date:  2003-01-20       Impact factor: 15.336

4.  An efficient, stereocontrolled synthesis of a potent omuralide-salinosporin hybrid for selective proteasome inhibition.

Authors:  Leleti Rajender Reddy; Jean-François Fournier; B V Subba Reddy; E J Corey
Journal:  J Am Chem Soc       Date:  2005-06-29       Impact factor: 15.419

Review 5.  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

6.  Biosynthetic convergence of salinosporamides A and B in the marine actinomycete Salinispora tropica.

Authors:  Laura L Beer; Bradley S Moore
Journal:  Org Lett       Date:  2007-02-03       Impact factor: 6.005

7.  Crystal structures of Salinosporamide A (NPI-0052) and B (NPI-0047) in complex with the 20S proteasome reveal important consequences of beta-lactone ring opening and a mechanism for irreversible binding.

Authors:  Michael Groll; Robert Huber; Barbara C M Potts
Journal:  J Am Chem Soc       Date:  2006-04-19       Impact factor: 15.419

8.  Structure-activity relationship studies of salinosporamide A (NPI-0052), a novel marine derived proteasome inhibitor.

Authors:  Venkat R Macherla; Scott S Mitchell; Rama Rao Manam; Katherine A Reed; Ta-Hsiang Chao; Benjamin Nicholson; Gordafaried Deyanat-Yazdi; Bao Mai; Paul R Jensen; William F Fenical; Saskia T C Neuteboom; Kin S Lam; Michael A Palladino; Barbara C M Potts
Journal:  J Med Chem       Date:  2005-06-02       Impact factor: 7.446

Review 9.  A novel proteasome inhibitor NPI-0052 as an anticancer therapy.

Authors:  D Chauhan; T Hideshima; K C Anderson
Journal:  Br J Cancer       Date:  2006-10-23       Impact factor: 7.640

10.  Discovery and characterization of a marine bacterial SAM-dependent chlorinase.

Authors:  Alessandra S Eustáquio; Florence Pojer; Joseph P Noel; Bradley S Moore
Journal:  Nat Chem Biol       Date:  2007-12-02       Impact factor: 15.040
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  24 in total

Review 1.  Salinosporamide natural products: Potent 20 S proteasome inhibitors as promising cancer chemotherapeutics.

Authors:  Tobias A M Gulder; Bradley S Moore
Journal:  Angew Chem Int Ed Engl       Date:  2010-12-03       Impact factor: 15.336

2.  An approach to the site-selective deoxygenation of hydroxy groups based on catalytic phosphoramidite transfer.

Authors:  Peter A Jordan; Scott J Miller
Journal:  Angew Chem Int Ed Engl       Date:  2012-02-08       Impact factor: 15.336

Review 3.  Genomic basis for natural product biosynthetic diversity in the actinomycetes.

Authors:  Markus Nett; Haruo Ikeda; Bradley S Moore
Journal:  Nat Prod Rep       Date:  2009-09-01       Impact factor: 13.423

4.  Bacterial self-resistance to the natural proteasome inhibitor salinosporamide A.

Authors:  Andrew J Kale; Ryan P McGlinchey; Anna Lechner; Bradley S Moore
Journal:  ACS Chem Biol       Date:  2011-09-26       Impact factor: 5.100

5.  Prephenate decarboxylases: a new prephenate-utilizing enzyme family that performs nonaromatizing decarboxylation en route to diverse secondary metabolites.

Authors:  Sarah Mahlstedt; Elisha N Fielding; Bradley S Moore; Christopher T Walsh
Journal:  Biochemistry       Date:  2010-10-26       Impact factor: 3.162

6.  Engineering fluorometabolite production: fluorinase expression in Salinispora tropica Yields Fluorosalinosporamide.

Authors:  Alessandra S Eustáquio; David O'Hagan; Bradley S Moore
Journal:  J Nat Prod       Date:  2010-03-26       Impact factor: 4.050

7.  Biosynthesis of salinosporamides from alpha,beta-unsaturated fatty acids: implications for extending polyketide synthase diversity.

Authors:  Yuan Liu; Christopher Hazzard; Alessandra S Eustáquio; Kevin A Reynolds; Bradley S Moore
Journal:  J Am Chem Soc       Date:  2009-08-05       Impact factor: 15.419

Review 8.  Antitumor compounds from marine actinomycetes.

Authors:  Carlos Olano; Carmen Méndez; José A Salas
Journal:  Mar Drugs       Date:  2009-06-11       Impact factor: 5.118

Review 9.  Generating a generation of proteasome inhibitors: from microbial fermentation to total synthesis of salinosporamide a (marizomib) and other salinosporamides.

Authors:  Barbara C Potts; Kin S Lam
Journal:  Mar Drugs       Date:  2010-03-25       Impact factor: 5.118

10.  Coupled Biosynthesis of Volatiles and Salinosporamide A in Salinispora tropica.

Authors:  Ulrike Groenhagen; Ana Ligia Leandrini De Oliveira; Elisha Fielding; Bradley S Moore; Stefan Schulz
Journal:  Chembiochem       Date:  2016-09-06       Impact factor: 3.164
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