Synthesis-Driven Stereochemical Assignment of Marine Polycyclic Ether Natural Products.
Aquatic Organisms
/ metabolism
Chemistry Techniques, Synthetic
Ciguatoxins
/ chemical synthesis
Ethers
/ chemical synthesis
Ethers, Cyclic
/ chemical synthesis
Humans
Magnetic Resonance Spectroscopy
Marine Toxins
/ chemical synthesis
Molecular Structure
Oxocins
/ chemical synthesis
Polymers
/ chemical synthesis
Secondary Metabolism
Stereoisomerism
Structure-Activity Relationship
NMR spectroscopic analysis
chemical shift deviation analysis
dinoflagellates
neurotoxins
partial synthesis
polycyclic ethers
secondary metabolites
total synthesis
Journal
Marine drugs
ISSN: 1660-3397
Titre abrégé: Mar Drugs
Pays: Switzerland
ID NLM: 101213729
Informations de publication
Date de publication:
29 Apr 2021
29 Apr 2021
Historique:
received:
09
04
2021
revised:
26
04
2021
accepted:
27
04
2021
entrez:
5
5
2021
pubmed:
6
5
2021
medline:
27
5
2021
Statut:
epublish
Résumé
Marine polycyclic ether natural products have gained significant interest from the chemical community due to their impressively huge molecular architecture and diverse biological functions. The structure assignment of this class of extraordinarily complex natural products has mainly relied on NMR spectroscopic analysis. However, NMR spectroscopic analysis has its own limitations, including configurational assignment of stereogenic centers within conformationally flexible systems. Chemical shift deviation analysis of synthetic model compounds is a reliable means to assign the relative configuration of "difficult" stereogenic centers. The complete configurational assignment must be ultimately established through total synthesis. The aim of this review is to summarize the indispensable role of organic synthesis in stereochemical assignment of marine polycyclic ethers.
Identifiants
pubmed: 33947080
pii: md19050257
doi: 10.3390/md19050257
pmc: PMC8145320
pii:
doi:
Substances chimiques
Ethers
0
Ethers, Cyclic
0
Marine Toxins
0
Oxocins
0
Polymers
0
brevenal (polyether)
0
Ciguatoxins
11050-21-8
maitotoxin
9P59GES78D
Types de publication
Journal Article
Review
Langues
eng
Sous-ensembles de citation
IM
Subventions
Organisme : Chuo University
ID : Personal Research Grant
Références
Chem Rec. 2010 Jun;10(3):159-72
pubmed: 20503205
Mar Drugs. 2017 Jul 20;15(7):
pubmed: 28726749
Nat Prod Rep. 2009 Sep;26(9):1105-24
pubmed: 19693411
Front Pharmacol. 2020 May 15;11:735
pubmed: 32499709
Chem Soc Rev. 2012 Feb 7;41(3):988-99
pubmed: 21796323
J Biol Chem. 1982 Jul 10;257(13):7287-89
pubmed: 6282837
Cell Signal. 2001 Oct;13(10):711-6
pubmed: 11602181
J Neurochem. 1998 Jan;70(1):409-16
pubmed: 9422388
J Biol Chem. 1983 Sep 25;258(18):10944-9
pubmed: 6309824
J Org Chem. 1999 Feb 5;64(3):866-876
pubmed: 11674159
J Am Chem Soc. 2012 Mar 14;134(10):4963-8
pubmed: 22372917
Chemistry. 2019 Jun 26;25(36):8528-8542
pubmed: 30882926
Bioorg Med Chem. 2011 Nov 15;19(22):6675-701
pubmed: 21715178
Chem Rec. 2001;1(3):228-42
pubmed: 11895121
Angew Chem Int Ed Engl. 2011 Jul 18;50(30):6722-37
pubmed: 21618370
Angew Chem Int Ed Engl. 2007;46(46):8875-9
pubmed: 17943950
Chemistry. 2013 Apr 22;19(17):5276-88
pubmed: 23554126
J Am Chem Soc. 2010 Sep 22;132(37):12946-59
pubmed: 20795713
J Am Chem Soc. 2008 Jun 11;130(23):7466-76
pubmed: 18481856
Jpn J Pharmacol. 2001 Jan;85(1):98-100
pubmed: 11243582
Nat Prod Rep. 2008 Apr;25(2):401-26
pubmed: 18389143
Toxicon. 2010 Oct;56(5):792-6
pubmed: 19682481
Mar Drugs. 2009 Jul 13;7(3):314-30
pubmed: 19841716
Angew Chem Int Ed Engl. 2000 Dec 1;39(23):4279-4281
pubmed: 29711895
Br J Pharmacol. 1985 Oct;86(2):385-91
pubmed: 2996678
Angew Chem Int Ed Engl. 2000 Dec 1;39(23):4282-4284
pubmed: 29711890
J Am Chem Soc. 2012 Jul 25;134(29):11984-7
pubmed: 22779404
Angew Chem Int Ed Engl. 2006 Jul 3;45(27):4406-13
pubmed: 16767782
J Am Chem Soc. 2001 Mar 7;123(9):2076-8
pubmed: 11456839
Angew Chem Int Ed Engl. 2004 Jan;43(1):81-4
pubmed: 14694477
Angew Chem Int Ed Engl. 2018 Mar 26;57(14):3801-3805
pubmed: 29385300
Nat Prod Rep. 2000 Jun;17(3):293-314
pubmed: 10888014
Chem Soc Rev. 2008 Jun;37(6):1218-28
pubmed: 18497934
Science. 2007 Aug 31;317(5842):1189-92
pubmed: 17761875
Acc Chem Res. 2020 Sep 15;53(9):1922-1932
pubmed: 32794691
J Am Chem Soc. 2006 Aug 2;128(30):9648-50
pubmed: 16866516
Mar Drugs. 2020 Mar 20;18(3):
pubmed: 32245015
Angew Chem Int Ed Engl. 2005 Feb 4;44(7):1012-1044
pubmed: 15688428
J Org Chem. 2009 Jun 5;74(11):4024-40
pubmed: 19422179
Org Lett. 2008 Jun 5;10(11):2275-8
pubmed: 18444658
J Am Chem Soc. 2005 Apr 6;127(13):4685-96
pubmed: 15796535
J Nat Prod. 2005 Jan;68(1):2-6
pubmed: 15679307
Am J Respir Crit Care Med. 2005 Jan 1;171(1):26-34
pubmed: 15447946
Org Lett. 2008 Jun 5;10(11):2211-4
pubmed: 18476664
Org Lett. 2015 May 15;17(10):2392-5
pubmed: 25950201
J Med Chem. 1989 Jan;32(1):197-202
pubmed: 2909732
PLoS One. 2008;3(10):e3448
pubmed: 18941627
Chemistry. 2011 Dec 2;17(49):13754-61
pubmed: 22052481
Toxicon. 1985;23(3):473-9
pubmed: 3895583
J Am Chem Soc. 2002 Dec 18;124(50):14983-92
pubmed: 12475341
J Org Chem. 1997 Oct 17;62(21):7507
pubmed: 11671877
J Am Chem Soc. 2006 Dec 27;128(51):16989-99
pubmed: 17177450
Toxicon. 2003 Mar;41(4):469-74
pubmed: 12657316
Angew Chem Int Ed Engl. 2007;46(28):5278-82
pubmed: 17469088
Toxicon. 2007 Feb;49(2):124-41
pubmed: 17239913
Org Lett. 2004 Apr 29;6(9):1501-4
pubmed: 15101777
Chem Rev. 2012 Mar 14;112(3):1839-62
pubmed: 22091891