The occurrence of ansamers in the synthesis of cyclic peptides.
Journal
Nature communications
ISSN: 2041-1723
Titre abrégé: Nat Commun
Pays: England
ID NLM: 101528555
Informations de publication
Date de publication:
30 10 2022
30 10 2022
Historique:
received:
20
05
2022
accepted:
14
10
2022
entrez:
31
10
2022
pubmed:
1
11
2022
medline:
2
11
2022
Statut:
epublish
Résumé
α-Amanitin is a bicyclic octapeptide composed of a macrolactam with a tryptathionine cross-link forming a handle. Previously, the occurrence of isomers of amanitin, termed atropisomers has been postulated. Although the total synthesis of α-amanitin has been accomplished this aspect still remains unsolved. We perform the synthesis of amanitin analogs, accompanied by in-depth spectroscopic, crystallographic and molecular dynamics studies. The data unambiguously confirms the synthesis of two amatoxin-type isomers, for which we propose the term ansamers. The natural structure of the P-ansamer can be ansa-selectively synthesized using an optimized synthetic strategy. We believe that the here described terminology does also have implications for many other peptide structures, e.g. norbornapeptides, lasso peptides, tryptorubins and others, and helps to unambiguously describe conformational isomerism of cyclic peptides.
Identifiants
pubmed: 36310176
doi: 10.1038/s41467-022-34125-8
pii: 10.1038/s41467-022-34125-8
pmc: PMC9618573
doi:
Substances chimiques
Alpha-Amanitin
0
Peptides, Cyclic
0
Amanitins
0
Peptides
0
Types de publication
Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
6488Subventions
Organisme : NIGMS NIH HHS
ID : P41 GM103311
Pays : United States
Informations de copyright
© 2022. The Author(s).
Références
Proteins. 2005 Jun 1;59(4):687-96
pubmed: 15815974
Nat Struct Mol Biol. 2008 Aug;15(8):811-8
pubmed: 18552824
Chemistry. 2008;14(11):3410-7
pubmed: 18307186
J Am Chem Soc. 2021 Sep 8;143(35):14322-14331
pubmed: 34459587
J Org Chem. 2005 Jun 10;70(12):4578-84
pubmed: 15932292
Angew Chem Int Ed Engl. 2020 Mar 27;59(14):5500-5504
pubmed: 31846557
Science. 1970 Oct 23;170(3956):447-9
pubmed: 4918258
Chem Biol. 2014 Dec 18;21(12):1610-7
pubmed: 25484237
Nat Chem. 2018 Jun;10(6):615-624
pubmed: 29784991
J Comput Chem. 2005 Dec;26(16):1701-18
pubmed: 16211538
Angew Chem Int Ed Engl. 2001 Feb 16;40(4):701-704
pubmed: 11241596
Nat Chem. 2021 Mar;13(3):218-225
pubmed: 33589789
Chemistry. 2019 Jun 18;25(34):8030-8034
pubmed: 31034701
J Comput Chem. 2004 Oct;25(13):1605-12
pubmed: 15264254
Chemistry. 2001 Nov 5;7(21):4665-73
pubmed: 11757659
Science. 2020 Jan 24;367(6476):458-463
pubmed: 31896661
BMC Res Notes. 2012 Jul 23;5:367
pubmed: 22824207
Chem Rev. 1996 Oct 1;96(6):2097-2112
pubmed: 11848823
J Am Chem Soc. 2008 Aug 27;130(34):11446-54
pubmed: 18671394
Angew Chem Int Ed Engl. 2007;46(19):3547-9
pubmed: 17385816
Angew Chem Int Ed Engl. 2020 Jul 6;59(28):11390-11393
pubmed: 32091645
Biopolymers. 2007;88(5):714-24
pubmed: 17626299
J Am Chem Soc. 2018 May 30;140(21):6513-6517
pubmed: 29561592
Nat Commun. 2017 Oct 19;8(1):1045
pubmed: 29051530
J Biomol NMR. 2015 Sep;63(1):21-37
pubmed: 26123317
Nat Chem. 2021 Sep;13(9):850-857
pubmed: 34426684
J Org Chem. 2019 May 3;84(9):5271-5276
pubmed: 30945543
Int J Pept Protein Res. 1992 Dec;40(6):551-8
pubmed: 1286940
Chem Sci. 2015 Oct 1;6(10):5473-5490
pubmed: 29861888