Evidence map›Paper›PMID 29296671›Full record

ArticleACS central science2017

Synthesis of Diverse 11- and 12-Membered Macrolactones from a Common Linear Substrate Using a Single Biocatalyst.

Michael M Gilbert, Matthew D DeMars, Song Yang, Jessica M Grandner, Shoulei Wang, Hengbin Wang, Alison R H Narayan, David H Sherman, K N Houk, John Montgomery

Abstract read
In one paragraph

Article in ACS central science, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.

0numbers the graph read from it
0cells of the map it votes in
11citing papers in PubMed
–field-weighted citation impact
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

11 citing papers in PubMed.

  1. Article
  2. Engineered and Artificial Metalloenzymes for Selective C-H Functionalization.Current opinion in green and sustainable chemistry · 2021
    Article
  3. Late-Stage Intermolecular Allylic C-H Amination.Journal of the American Chemical Society · 2021
    Article
  4. Enzymkatalysierte späte Modifizierungen: Besser spät als nie.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2021
    Review
  5. Enzymatic Late-Stage Modifications: Better Late Than Never.Angewandte Chemie (International ed. in English) · 2021
    Review
  6. Exploration of Iron- and a-Ketoglutarate-Dependent Dioxygenases as Practical Biocatalysts in Natural Product Synthesis.Synlett : accounts and rapid communications in synthetic organic chemistry · 2021
    Article
  7. ACS central science · 2019
    Article
  8. Review
  9. Review
  10. Article
  11. Review
4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

10 authors.

Michael M GilbertDepartment of Chemistry, University of Michigan, Ann Arbor, Michigan 48109-1055, United States.
Matthew D DeMarsLife Sciences Institute, University of Michigan, Ann Arbor, Michigan 48109, United States.
Song YangDepartment of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, United States.
Jessica M GrandnerDepartment of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, United States.
Shoulei WangDepartment of Chemistry, University of Michigan, Ann Arbor, Michigan 48109-1055, United States.
Hengbin WangDepartment of Chemistry, University of Michigan, Ann Arbor, Michigan 48109-1055, United States.
Alison R H NarayanDepartment of Chemistry, University of Michigan, Ann Arbor, Michigan 48109-1055, United States.
David H ShermanDepartment of Chemistry, University of Michigan, Ann Arbor, Michigan 48109-1055, United States.
K N HoukDepartment of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, United States.
John MontgomeryDepartment of Chemistry, University of Michigan, Ann Arbor, Michigan 48109-1055, United States.

Funding

Supplement: Regio- and Site-Selective Processes Using Transition Metal and Biological CatalystsR35GM118133 · NIGMS · UNIVERSITY OF MICHIGAN AT ANN ARBOR · PI JOHN MONTGOMERY · 2016 to 2026
$4.9M
Discovery and Characterization of Natural Product Systems-Research Supplement to Promote DiversityR35GM118101 · NIGMS · UNIVERSITY OF MICHIGAN AT ANN ARBOR · PI SHERMAN, DAVID H · 2016 to 2025
$3.3M
Cellular Biotechnology Training Program (CBTP) - Years 31-35T32GM145304 · NIGMS · UNIVERSITY OF MICHIGAN AT ANN ARBOR · PI Guizhi Zhu · 2022 to 2026
$2.6M
NIGMS NIH HHS R35 GM118101NIGMS NIH HHS R35 GM118133NIGMS NIH HHS T32 GM145304
6 · The paper itself

Abstract

The diversification of late stage synthetic intermediates provides significant advantages in efficiency in comparison to conventional linear approaches. Despite these advantages, accessing varying ring scaffolds and functional group patterns from a common intermediate poses considerable challenges using existing methods. The combination of regiodivergent nickel-catalyzed C-C couplings and site-selective biocatalytic C-H oxidations using the cytochrome P450 enzyme PikC addresses this problem by enabling a single late-stage linear intermediate to be converted to macrolactones of differing ring size and with diverse patterns of oxidation. The approach is made possible by a novel strategy for site-selective biocatalytic oxidation using a single biocatalyst, with site selectivity being governed by a temporarily installed directing group. Site selectivities of C-H oxidation by this directed approach can overcome positional bias due to C-H bond strength, acidity, inductive influences, steric accessibility, or immediate proximity to the directing group, thus providing complementarity to existing approaches.

Identifiers

PMID29296671
PMCPMC5746868

What OpenQuestion holds

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Registered trials

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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.