Solid-Phase Synthesis of Head to Side-Chain Tyr-Cyclodepsipeptides Through a Cyclative Cleavage From Fmoc-MeDbz/MeNbz-resins.

cyclothiodepsipeptides heterodetic cyclic peptides homodetic cyclic peptides native chemical ligation solid-phase peptide synthesis

Journal

Frontiers in chemistry
ISSN: 2296-2646
Titre abrégé: Front Chem
Pays: Switzerland
ID NLM: 101627988

Informations de publication

Date de publication:
2020
Historique:
received: 11 02 2020
accepted: 25 03 2020
entrez: 12 5 2020
pubmed: 12 5 2020
medline: 12 5 2020
Statut: epublish

Résumé

Cyclic depsipeptides constitute a fascinating class of natural products. Most of them are characterized by an ester formed between the β-hydroxy function of Ser/Thr -and related amino acids- and the carboxylic group of the

Identifiants

pubmed: 32391324
doi: 10.3389/fchem.2020.00298
pmc: PMC7189019
doi:

Types de publication

Journal Article

Langues

eng

Pagination

298

Informations de copyright

Copyright © 2020 Acosta, Murray, Royo, de la Torre and Albericio.

Références

Angew Chem Int Ed Engl. 2018 Sep 3;57(36):11634-11639
pubmed: 29908104
Angew Chem Int Ed Engl. 2003 Jan 27;42(4):431-4
pubmed: 12569509
J Org Chem. 2018 Feb 16;83(4):1797-1803
pubmed: 29293336
Bioorg Med Chem. 2001 Sep;9(9):2479-84
pubmed: 11553489
Angew Chem Int Ed Engl. 2014 May 12;53(20):5194-8
pubmed: 24692304
Mar Drugs. 2013 May 21;11(5):1693-717
pubmed: 23697952
Acc Chem Res. 2019 Dec 17;52(12):3361-3371
pubmed: 31536331
Bioorg Med Chem. 2018 Jun 1;26(10):2914-2918
pubmed: 29735426
Chemistry. 2017 Sep 12;23(51):12484-12488
pubmed: 28741313
Org Lett. 2015 Jan 2;17(1):130-3
pubmed: 25506740
Angew Chem Int Ed Engl. 2018 Dec 3;57(49):16120-16125
pubmed: 30307096
J Comb Chem. 2006 Mar-Apr;8(2):213-20
pubmed: 16529516
Org Lett. 2018 Jul 20;20(14):4306-4309
pubmed: 29953237
J Org Chem. 2004 Jun 11;69(12):4145-51
pubmed: 15176841
Pharmaceuticals (Basel). 2020 Mar 05;13(3):
pubmed: 32151051
Angew Chem Int Ed Engl. 2014 May 12;53(20):5188-93
pubmed: 24644239
Chem Rev. 2011 Nov 9;111(11):6557-602
pubmed: 21866984
J Org Chem. 2018 Dec 21;83(24):15297-15311
pubmed: 30525634
Org Lett. 2016 Aug 19;18(16):4140-3
pubmed: 27494794
Org Biomol Chem. 2017 Mar 28;15(12):2491-2496
pubmed: 28170021
J Med Chem. 2019 Sep 12;62(17):8080-8089
pubmed: 31373811
J Am Chem Soc. 2017 Mar 22;139(11):3946-3949
pubmed: 28230996
J Am Chem Soc. 2013 Feb 27;135(8):3173-85
pubmed: 23343390
Chembiochem. 2014 May 5;15(7):946-9
pubmed: 24623714
Molecules. 2020 Feb 09;25(3):
pubmed: 32050446
Bioorg Med Chem. 2018 Jun 1;26(10):2700-2707
pubmed: 28720325
J Med Chem. 2018 Feb 22;61(4):1382-1414
pubmed: 28737935
Angew Chem Int Ed Engl. 2008;47(36):6851-5
pubmed: 18651678
Chem Sci. 2017 Aug 1;8(8):5362-5370
pubmed: 28970915
Chem Commun (Camb). 2016 May 25;52(42):6911-3
pubmed: 27146590
Chem Sci. 2017 Nov 9;9(2):350-355
pubmed: 29629104
J Am Chem Soc. 2015 Jun 10;137(22):7197-209
pubmed: 25978693
Chemistry. 2009 Sep 21;15(37):9394-403
pubmed: 19575348
Chem Commun (Camb). 2020 Jan 21;56(6):956-959
pubmed: 31858094
J Bacteriol. 2003 Dec;185(24):7036-43
pubmed: 14645262
Future Med Chem. 2009 May;1(2):361-77
pubmed: 21425973
Org Lett. 2018 Dec 7;20(23):7616-7619
pubmed: 30421931
Science. 1994 Nov 4;266(5186):776-9
pubmed: 7973629
J Org Chem. 2019 Jan 18;84(2):1035-1041
pubmed: 30566351
J Org Chem. 2018 Sep 7;83(17):10525-10534
pubmed: 30079722
Chem Rev. 2009 Jun;109(6):2455-504
pubmed: 19364121
Org Lett. 2017 Oct 6;19(19):5276-5279
pubmed: 28952740

Auteurs

Gerardo A Acosta (GA)

CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, University of Barcelona (UB), Barcelona, Spain.
Department of Organic Chemistry, University of Barcelona, Barcelona, Spain.
Institute of Advanced Chemistry of Catalonia (IQAC-CSIC), Spanish National Research Council (CSIC), Barcelona, Spain.
Associated Unit, Spanish National Research Council-University of Barcelona (CSIC-UB), Barcelona, Spain.

Laura Murray (L)

CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, University of Barcelona (UB), Barcelona, Spain.
Department of Organic Chemistry, University of Barcelona, Barcelona, Spain.

Miriam Royo (M)

Institute of Advanced Chemistry of Catalonia (IQAC-CSIC), Spanish National Research Council (CSIC), Barcelona, Spain.
Associated Unit, Spanish National Research Council-University of Barcelona (CSIC-UB), Barcelona, Spain.

Beatriz G de la Torre (BG)

KwaZulu-Natal Research Innovation and Sequencing Platform (KRISP), School of Laboratory Medicine and Medical Sciences, College of Health Sciences, University of KwaZulu-Natal, Durban, South Africa.
Peptide Science Laboratory, School of Chemistry and Physics, University of KwaZulu-Natal, Durban, South Africa.

Fernando Albericio (F)

CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, University of Barcelona (UB), Barcelona, Spain.
Department of Organic Chemistry, University of Barcelona, Barcelona, Spain.
Institute of Advanced Chemistry of Catalonia (IQAC-CSIC), Spanish National Research Council (CSIC), Barcelona, Spain.
Associated Unit, Spanish National Research Council-University of Barcelona (CSIC-UB), Barcelona, Spain.
Peptide Science Laboratory, School of Chemistry and Physics, University of KwaZulu-Natal, Durban, South Africa.

Classifications MeSH