Literature DB >> 32052896

Control of Stereoselectivity in Diverse Hapalindole Metabolites is Mediated by Cofactor-Induced Combinatorial Pairing of Stig Cyclases.

Shasha Li1, Sean A Newmister2, Andrew N Lowell2,3, Jiachen Zi4, Callie R Chappell5, Fengan Yu2, Robert M Hohlman1, Jimmy Orjala4, Robert M Williams6,7, David H Sherman8.   

Abstract

Stereospecific polycyclic core formation of hapalindoles and fischerindoles is controlled by Stig cyclases through a three-step cascade involving Cope rearrangement, 6-exo-trig cyclization, and a final electrophilic aromatic substitution. Reported here is a comprehensive study of all currently annotated Stig cyclases, revealing that these proteins can assemble into heteromeric complexes, induced by Ca2+ , to cooperatively control the stereochemistry of hapalindole natural products.
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  biocatalysis; cyclases; indoles; oligomerization; rearrangements

Mesh：

Substances：

Year:  2020        PMID： 32052896      PMCID： PMC7274885          DOI： 10.1002/anie.201913686

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  19 in total

1.  Antimicrobial ambiguine isonitriles from the cyanobacterium Fischerella ambigua.

Authors:  Shunyan Mo; Aleksej Krunic; George Chlipala; Jimmy Orjala
Journal:  J Nat Prod       Date:  2009-05-22       Impact factor: 4.050

Review 2.  Advances in high-resolution cryo-EM of oligomeric enzymes.

Authors:  Janet Vonck; Deryck J Mills
Journal:  Curr Opin Struct Biol       Date:  2017-07-17       Impact factor: 6.809

3.  Identification and characterization of a welwitindolinone alkaloid biosynthetic gene cluster in the stigonematalean Cyanobacterium Hapalosiphon welwitschii.

Authors:  Matthew L Hillwig; Heather A Fuhrman; Kuljira Ittiamornkul; Tyler J Sevco; Daniel H Kwak; Xinyu Liu
Journal:  Chembiochem       Date:  2014-03-21       Impact factor: 3.164

4.  Discovery of a Calcium-Dependent Enzymatic Cascade for the Selective Assembly of Hapalindole-Type Alkaloids: On the Biosynthetic Origin of Hapalindole U.

Authors:  Qin Zhu; Xinyu Liu
Journal:  Angew Chem Int Ed Engl       Date:  2017-06-29       Impact factor: 15.336

5.  Structural basis of the Cope rearrangement and cyclization in hapalindole biogenesis.

Authors:  Sean A Newmister; Shasha Li; Marc Garcia-Borràs; Jacob N Sanders; Song Yang; Andrew N Lowell; Fengan Yu; Janet L Smith; Robert M Williams; K N Houk; David H Sherman
Journal:  Nat Chem Biol       Date:  2018-03-12       Impact factor: 15.040

6.  Antimicrobial ambiguines from the cyanobacterium Fischerella sp. collected in Israel.

Authors:  Avi Raveh; Shmuel Carmeli
Journal:  J Nat Prod       Date:  2007-02       Impact factor: 4.050

7.  The Chemistry of Hapalindoles, Fischerindoles, Ambiguines, and Welwitindolinones.

Authors:  Vikram Bhat; Apurva Dave; James A MacKay; Viresh H Rawal
Journal:  Alkaloids Chem Biol       Date:  2013-12-25

8.  Total synthesis of hapalindole-type natural products.

Authors:  Zhaohong Lu; Ming Yang; Pengxi Chen; Xiaochun Xiong; Ang Li
Journal:  Angew Chem Int Ed Engl       Date:  2014-10-10       Impact factor: 15.336

9.  The Crystal Structure of a Class of Cyclases that Catalyze the Cope Rearrangement.

Authors:  Chun-Chi Chen; Xiangying Hu; Xueke Tang; Yunyun Yang; Tzu-Ping Ko; Jian Gao; Yingying Zheng; Jian-Wen Huang; Zhengsen Yu; Liping Li; Shuai Han; Ningning Cai; Yonghui Zhang; Weidong Liu; Rey-Ting Guo
Journal:  Angew Chem Int Ed Engl       Date:  2018-10-23       Impact factor: 15.336

10.  Decoding cyclase-dependent assembly of hapalindole and fischerindole alkaloids.

Authors:  Shasha Li; Andrew N Lowell; Sean A Newmister; Fengan Yu; Robert M Williams; David H Sherman
Journal:  Nat Chem Biol       Date:  2017-03-13       Impact factor: 15.040
View more
  1 in total

Review 1.  Recent advances in hapalindole-type cyanobacterial alkaloids: biosynthesis, synthesis, and biological activity.

Authors:  Robert M Hohlman; David H Sherman
Journal:  Nat Prod Rep       Date:  2021-09-23       Impact factor: 15.111
  1 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.