Predictive Engineering of Class I Terpene Synthases Using Experimental and Computational Approaches.
computational chemistry
functional plasticity
protein engineering
terpene synthases
terpenoids
Journal
Chembiochem : a European journal of chemical biology
ISSN: 1439-7633
Titre abrégé: Chembiochem
Pays: Germany
ID NLM: 100937360
Informations de publication
Date de publication:
04 03 2022
04 03 2022
Historique:
revised:
15
10
2021
received:
14
09
2021
pubmed:
21
10
2021
medline:
26
4
2022
entrez:
20
10
2021
Statut:
ppublish
Résumé
Terpenoids are a highly diverse group of natural products with considerable industrial interest. Increasingly, engineered microbes are used for the production of terpenoids to replace natural extracts and chemical synthesis. Terpene synthases (TSs) show a high level of functional plasticity and are responsible for the vast structural diversity observed in natural terpenoids. Their relatively inert active sites guide intrinsically reactive linear carbocation intermediates along one of many cyclisation paths via exertion of subtle steric and electrostatic control. Due to the absence of a strong protein interaction with these intermediates, there is a remarkable lack of sequence-function relationship within the TS family, making product-outcome predictions from sequences alone challenging. This, in combination with the fact that many TSs produce multiple products from a single substrate hampers the design and use of TSs in the biomanufacturing of terpenoids. This review highlights recent advances in genome mining, computational modelling, high-throughput screening, and machine-learning that will allow more predictive engineering of these fascinating enzymes in the near future.
Identifiants
pubmed: 34669250
doi: 10.1002/cbic.202100484
pmc: PMC9298401
doi:
Substances chimiques
Terpenes
0
Alkyl and Aryl Transferases
EC 2.5.-
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Review
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202100484Informations de copyright
© 2021 The Authors. ChemBioChem published by Wiley-VCH GmbH.
Références
Metab Eng. 2017 Jul;42:1-8
pubmed: 28438645
Angew Chem Int Ed Engl. 2020 Jul 13;59(29):11943-11947
pubmed: 32342621
Plant J. 2011 Apr;66(1):212-29
pubmed: 21443633
J Am Chem Soc. 2002 Jul 24;124(29):8546-7
pubmed: 12121093
Proc Natl Acad Sci U S A. 2008 May 27;105(21):7422-7
pubmed: 18492804
J Antibiot (Tokyo). 1980 Jan;33(1):92-3
pubmed: 7372558
Arch Biochem Biophys. 2003 Sep 15;417(2):203-11
pubmed: 12941302
Angew Chem Int Ed Engl. 2017 Dec 18;56(51):16385-16389
pubmed: 29125678
Nat Chem Biol. 2008 Oct;4(10):617-23
pubmed: 18776889
Bioresour Technol. 2020 Mar;300:122666
pubmed: 31901556
ACS Catal. 2017 Jan 6;7(1):812-818
pubmed: 29399379
Arch Biochem Biophys. 2005 Jul 15;439(2):222-33
pubmed: 15978541
Biochemistry. 2018 Apr 3;57(13):1997-2008
pubmed: 29533655
Angew Chem Int Ed Engl. 2021 Jun 14;60(25):14163-14170
pubmed: 33780586
Biochemistry. 2017 Mar 28;56(12):1706-1715
pubmed: 28272875
PLoS One. 2020 Apr 30;15(4):e0232220
pubmed: 32353014
Angew Chem Int Ed Engl. 2020 Nov 2;59(45):19961-19965
pubmed: 32749032
Biochemistry. 2020 Sep 8;59(35):3271-3283
pubmed: 32786410
Proc Natl Acad Sci U S A. 2002 Nov 26;99(24):15375-80
pubmed: 12432096
PLoS Comput Biol. 2021 Mar 22;17(3):e1008197
pubmed: 33750949
Front Plant Sci. 2016 Jul 12;7:1019
pubmed: 27462341
ACS Catal. 2019 Oct 4;9(10):8867-8871
pubmed: 32489716
Plant Cell. 2007 Jun;19(6):1994-2005
pubmed: 17557809
ChemistrySelect. 2016 Jun 21;1(9):1893-1896
pubmed: 29756025
Angew Chem Int Ed Engl. 2021 Sep 13;60(38):20781-20785
pubmed: 34318977
J Chem Theory Comput. 2019 Sep 10;15(9):5116-5134
pubmed: 31386808
Proc Natl Acad Sci U S A. 2001 Nov 20;98(24):13543-8
pubmed: 11698643
Proc Natl Acad Sci U S A. 1996 Jun 25;93(13):6841-5
pubmed: 8692906
Nat Prod Rep. 2020 Mar 25;37(3):425-463
pubmed: 31650156
Proc Natl Acad Sci U S A. 2015 Mar 17;112(11):3332-7
pubmed: 25733883
Chem Soc Rev. 2021 Jul 21;50(14):8003-8049
pubmed: 34142684
Arch Biochem Biophys. 2000 Apr 15;376(2):354-64
pubmed: 10775423
ACS Synth Biol. 2018 Oct 19;7(10):2379-2390
pubmed: 30261142
Nat Prod Rep. 2018 Dec 12;35(12):1330-1346
pubmed: 29855001
Microb Cell Fact. 2013 Aug 23;12:76
pubmed: 23968454
Proc Natl Acad Sci U S A. 2007 Mar 27;104(13):5360-5
pubmed: 17372193
Chembiochem. 2021 Jul 1;22(13):2325-2334
pubmed: 33938632
Sci Rep. 2019 Aug 15;9(1):11936
pubmed: 31417136
Biotechnol Bioeng. 2017 Aug;114(8):1703-1712
pubmed: 28369701
J Biol Chem. 1990 Aug 5;265(22):13157-64
pubmed: 2198286
J Biol Chem. 1994 Mar 18;269(11):8022-8
pubmed: 8132524
Phytochemistry. 2017 May;137:34-41
pubmed: 28215610
ACS Catal. 2018 Apr 6;8(4):3322-3330
pubmed: 30034923
ACS Synth Biol. 2019 Feb 15;8(2):232-238
pubmed: 30648856
Curr Opin Biotechnol. 2020 Oct;65:248-258
pubmed: 32679412
PLoS One. 2014 Mar 28;9(3):e93317
pubmed: 24681801
Chembiochem. 2019 Mar 15;20(6):785-792
pubmed: 30431225
J Biol Chem. 1993 Dec 25;268(36):26983-9
pubmed: 8262934
Chem Rev. 2006 Aug;106(8):3412-42
pubmed: 16895335
Beilstein J Org Chem. 2016 Nov 4;12:2317-2324
pubmed: 28144299
J Biol Chem. 1998 Jun 12;273(24):14891-9
pubmed: 9614092
J Biol Chem. 2014 Aug 22;289(34):23859-69
pubmed: 25016016
Structure. 1998 Feb 15;6(2):127-33
pubmed: 9519404
Cell. 2016 Mar 10;164(6):1185-1197
pubmed: 26967285
Methods Enzymol. 2012;515:123-62
pubmed: 22999173
Chembiochem. 2014 Jan 24;15(2):213-6
pubmed: 24399794
J Antibiot (Tokyo). 1969 Oct;22(10):508-9
pubmed: 5350510
Chembiochem. 2020 Apr 1;21(7):985-990
pubmed: 31682055
Nature. 2021 Aug;596(7873):583-589
pubmed: 34265844
Proc Natl Acad Sci U S A. 1997 Nov 25;94(24):12833-8
pubmed: 9371761
Nat Prod Rep. 2016 Jan;33(1):87-110
pubmed: 26563452
Angew Chem Int Ed Engl. 2014 Jul 14;53(29):7652-6
pubmed: 24890698
mBio. 2011 Jun 28;2(4):e00109-11
pubmed: 21712420
Biochemistry. 1996 Sep 24;35(38):12369-76
pubmed: 8823172
ACS Catal. 2017 Sep 1;7(9):6268-6282
pubmed: 28966840
Proc Natl Acad Sci U S A. 2015 Jan 20;112(3):857-62
pubmed: 25535391
Structure. 2011 Dec 7;19(12):1876-84
pubmed: 22153510
ACS Synth Biol. 2019 Jan 18;8(1):127-136
pubmed: 30563328
Metab Eng. 2013 Sep;19:33-41
pubmed: 23727191
Chembiochem. 2011 Sep 5;12(13):1988-91
pubmed: 21726035
Nat Prod Rep. 2015 Sep 23;32(10):1508-26
pubmed: 26216573
Org Biomol Chem. 2020 Jun 24;18(24):4547-4550
pubmed: 32253407
Science. 1997 Sep 19;277(5333):1815-20
pubmed: 9295271
Adv Biochem Eng Biotechnol. 2015;148:63-106
pubmed: 25583224
Science. 1997 Sep 19;277(5333):1820-4
pubmed: 9295272
Nature. 2006 Apr 20;440(7087):1078-82
pubmed: 16495946
ACS Catal. 2021 Feb 5;11(3):1033-1041
pubmed: 33614194
Curr Opin Chem Biol. 2014 Aug;21:25-33
pubmed: 24735749
Proc Natl Acad Sci U S A. 2019 Jan 8;116(2):506-511
pubmed: 30584096
Chem Rev. 2017 Sep 13;117(17):11570-11648
pubmed: 28841019
Biochemistry. 2017 Mar 28;56(12):1716-1725
pubmed: 28272876
Nat Commun. 2017 May 24;8:15526
pubmed: 28537253
Chembiochem. 2022 Mar 4;23(5):e202100484
pubmed: 34669250
MethodsX. 2014 Sep 08;1:187-96
pubmed: 26150952
Beilstein J Org Chem. 2019 Nov 29;15:2889-2906
pubmed: 31839835
J Am Chem Soc. 2020 Feb 12;142(6):2760-2765
pubmed: 31999448
J Appl Microbiol. 2015 Sep;119(3):605-19
pubmed: 26095690
Phytochemistry. 2009 Oct-Nov;70(15-16):1621-37
pubmed: 19793600
Proc Natl Acad Sci U S A. 2006 Jun 27;103(26):9826-31
pubmed: 16785438
ACS Catal. 2019 May 15;8(5):3780-3791
pubmed: 31157124
Nat Prod Rep. 2022 Jan 26;39(1):90-118
pubmed: 34231643
J Am Chem Soc. 2002 Jul 3;124(26):7681-9
pubmed: 12083921
Phytochemistry. 2019 Feb;158:157-165
pubmed: 30446165
Chembiochem. 2011 Nov 4;12(16):2403-7
pubmed: 21910204
Chembiochem. 2020 Mar 16;21(6):807-810
pubmed: 31553510
Angew Chem Int Ed Engl. 2021 Jan 18;60(3):1488-1492
pubmed: 33169911
Microb Cell Fact. 2019 Jun 8;18(1):105
pubmed: 31176369
Nature. 2012 Aug 16;488(7411):320-8
pubmed: 22895337
Acc Chem Res. 2012 Mar 20;45(3):463-72
pubmed: 22039990
Nat Biotechnol. 2003 Jul;21(7):796-802
pubmed: 12778056
Biotechnol J. 2014 Aug;9(8):1000-12
pubmed: 24756896
ACS Synth Biol. 2016 Sep 16;5(9):1011-20
pubmed: 27247193
Proc Natl Acad Sci U S A. 2015 May 5;112(18):5661-6
pubmed: 25901324
Arch Biochem Biophys. 2004 May 1;425(1):65-76
pubmed: 15081895
Chem Rev. 2021 Oct 27;121(20):12384-12444
pubmed: 34297541
Biochemistry. 2017 Oct 31;56(43):5798-5811
pubmed: 28967743
Chem Sci. 2016 Jul 1;7(7):4009-4015
pubmed: 30155043
J Chem Inf Model. 2020 Jun 22;60(6):2773-2790
pubmed: 32250622
Appl Microbiol. 1965 Nov;13(6):935-8
pubmed: 5866039