Literature DB >> 26160938

ORGANIC SYNTHESIS. Comment on "Asymmetric syntheses of sceptrin and massadine and evidence for biosynthetic enantiodivergence".

David H Sherman1, Sachiko Tsukamoto2, Robert M Williams3.   

Abstract

Ma et al. (Reports, 10 October 2014, p. 219) report asymmetric syntheses of sceptrin and massadine and, through a stereochemical reassignment, claim to "uncover enantiodivergence as a new biosynthetic paradigm for natural products." We challenge and clarify this claim with relevant examples from the literature of this well-known phenomenon of enantiodivergent congener biosynthesis within the same producing organism.
Copyright © 2015, American Association for the Advancement of Science.

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Year:  2015        PMID： 26160938      PMCID： PMC4499860          DOI： 10.1126/science.aaa9349

Source DB:  PubMed          Journal:  Science        ISSN： 0036-8075            Impact factor:   47.728


  12 in total

1.  C-O bond formation by polyketide synthases.

Authors:  Hyung-Jin Kwon; Wyatt C Smith; A Janelle Scharon; Sung Hee Hwang; Mark J Kurth; Ben Shen
Journal:  Science       Date:  2002-08-23       Impact factor: 47.728

Review 2.  Enantiomeric natural products: occurrence and biogenesis.

Authors:  Jennifer M Finefield; David H Sherman; Martin Kreitman; Robert M Williams
Journal:  Angew Chem Int Ed Engl       Date:  2012-05-03       Impact factor: 15.336

3.  Isolation, structure elucidation, and biomimetic total synthesis of versicolamide B, and the isolation of antipodal (-)-stephacidin A and (+)-notoamide B from Aspergillus versicolor NRRL 35600.

Authors:  Thomas J Greshock; Alan W Grubbs; Ping Jiao; Donald T Wicklow; James B Gloer; Robert M Williams
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

4.  Stereochemical diversity in lignan biosynthesis of Arctium lappa L.

Authors:  Shiro Suzuki; Toshiaki Umezawa; Mikio Shimada
Journal:  Biosci Biotechnol Biochem       Date:  2002-06       Impact factor: 2.043

5.  Diterpene synthases of the biosynthetic system of medicinally active diterpenoids in Marrubium vulgare.

Authors:  Philipp Zerbe; Angela Chiang; Harpreet Dullat; Mark O'Neil-Johnson; Courtney Starks; Björn Hamberger; Jörg Bohlmann
Journal:  Plant J       Date:  2014-07-23       Impact factor: 6.417

6.  Plant anticancer agents XXVII: Antileukemic and cytotoxic constituents of Dirca occidentalis (Thymelaeaceae).

Authors:  M M Badawi; S S Handa; A D Kinghorn; G A Cordell; N R Farnsworth
Journal:  J Pharm Sci       Date:  1983-11       Impact factor: 3.534

7.  Further novel metabolites of the paraherquamide family.

Authors:  S E Blanchflower; R M Banks; J R Everett; C Reading
Journal:  J Antibiot (Tokyo)       Date:  1993-09       Impact factor: 2.649

8.  Functional characterization of wheat ent-kaurene(-like) synthases indicates continuing evolution of labdane-related diterpenoid metabolism in the cereals.

Authors:  Ke Zhou; Meimei Xu; Mollie Tiernan; Qian Xie; Tomonobu Toyomasu; Chizu Sugawara; Madoka Oku; Masami Usui; Wataru Mitsuhashi; Makiko Chono; Peter M Chandler; Reuben J Peters
Journal:  Phytochemistry       Date:  2012-09-22       Impact factor: 4.072

9.  Identification and functional characterization of monofunctional ent-copalyl diphosphate and ent-kaurene synthases in white spruce reveal different patterns for diterpene synthase evolution for primary and secondary metabolism in gymnosperms.

Authors:  Christopher I Keeling; Harpreet K Dullat; Mack Yuen; Steven G Ralph; Sharon Jancsik; Jörg Bohlmann
Journal:  Plant Physiol       Date:  2009-12-31       Impact factor: 8.340

10.  Asymmetric syntheses of sceptrin and massadine and evidence for biosynthetic enantiodivergence.

Authors:  Zhiqiang Ma; Xiaolei Wang; Xiao Wang; Rodrigo A Rodriguez; Curtis E Moore; Shuanhu Gao; Xianghui Tan; Yuyong Ma; Arnold L Rheingold; Phil S Baran; Chuo Chen
Journal:  Science       Date:  2014-10-10       Impact factor: 47.728
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  3 in total

1.  ORGANIC SYNTHESIS. Response to Comment on "Asymmetric syntheses of sceptrin and massadine and evidence for biosynthetic enantiodivergence".

Authors:  Zhiqiang Ma; Xiaolei Wang; Xiao Wang; Rodrigo A Rodriguez; Curtis E Moore; Shuanhu Gao; Xianghui Tan; Yuyong Ma; Arnold L Rheingold; Phil S Baran; Chuo Chen
Journal:  Science       Date:  2015-07-09       Impact factor: 47.728

2.  Bisindole Alkaloids from a New Zealand Deep-Sea Marine Sponge Lamellomorpha strongylata.

Authors:  Kavita Ragini; Andrew M Piggott; Peter Karuso
Journal:  Mar Drugs       Date:  2019-12-04       Impact factor: 5.118

3.  Multilayer 3D Chirality and Its Synthetic Assembly.

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Journal:  Research (Wash D C)       Date:  2019-06-27
  3 in total

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