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Literature DB >> 33372776

Biosynthesis of the Immunosuppressant (-)-FR901483.

Zhuan Zhang, Yui Tamura¹, Mancheng Tang, Tianzhang Qiao, Michio Sato¹, Yoshihiro Otsu², Satoshi Sasamura², Masatoshi Taniguchi², Kenji Watanabe¹, Yi Tang.

Abstract

We report characterization of the biosynthetic pathway of the potent immunosuppressant (-)-FR901483 (1) through heterologous expression and enzymatic assays. The biosynthetic logic to form the azatricyclic alkaloid is consistent with those proposed in biomimetic syntheses and involves aza-spiro annulation of dityrosyl-piperazine to form a ketoaldehyde intermediate, followed by regioselective aldol condensation, stereoselective ketoreduction, and phosphorylation. A possible target of 1 is proposed based on the biosynthetic studies.

Entities: Chemical

Mesh：

Substances：

Year: 2020 PMID： 33372776 PMCID： PMC8094545 DOI： 10.1021/jacs.0c12352

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

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References

29 in total

1. Total synthesis of FR901483.

Authors: M Ousmer; N A Braun; M A Ciufolini
Journal: Org Lett Date: 2001-03-08 Impact factor: 6.005

2. A formal total synthesis of (-)-FR901483, using a tandem cationic aza-Cope rearrangement/Mannich cyclization approach.

Authors: Kay M Brummond; Sang-phyo Hong
Journal: J Org Chem Date: 2005-02-04 Impact factor: 4.354

3. Mechanism of the P450-Catalyzed Oxidative Cyclization in the Biosynthesis of Griseofulvin.

Authors: Jessica M Grandner; Ralph A Cacho; Yi Tang; K N Houk
Journal: ACS Catal Date: 2016-05-31 Impact factor: 13.084

4. A formal enantioselective total synthesis of FR901483.

Authors: Hao-Hua Huo; Hong-Kui Zhang; Xiao-Er Xia; Pei-Qiang Huang
Journal: Org Lett Date: 2012-08-31 Impact factor: 6.005

5. Rapid Syntheses of (-)-FR901483 and (+)-TAN1251C Enabled by Complexity-Generating Photocatalytic Olefin Hydroaminoalkylation.

Authors: Dominik Reich; Aaron Trowbridge; Matthew J Gaunt
Journal: Angew Chem Int Ed Engl Date: 2019-12-30 Impact factor: 15.336

Biosynthesis of the Immunosuppressant (-)-FR901483.

1. Total synthesis of FR901483.

2. A formal total synthesis of (-)-FR901483, using a tandem cationic aza-Cope rearrangement/Mannich cyclization approach.

3. Mechanism of the P450-Catalyzed Oxidative Cyclization in the Biosynthesis of Griseofulvin.

4. A formal enantioselective total synthesis of FR901483.

5. Rapid Syntheses of (-)-FR901483 and (+)-TAN1251C Enabled by Complexity-Generating Photocatalytic Olefin Hydroaminoalkylation.

6. Recent developments in self-resistance gene directed natural product discovery.

7. Total synthesis of the immunosuppressant FR901483 via an amidoacrolein cycloaddition.

8. Accumulation of 5-phosphoribosyl-1-pyrophosphate in human CCRF-CEM leukaemia cells treated with antifolates.

9. Spiro-ring formation is catalyzed by a multifunctional dioxygenase in austinol biosynthesis.

10. Studies on a total synthesis of the microbial immunosuppresive agent FR901483.