硫链丝菌素的全合成，第1部分：含脱氢哌啶/噻唑啉大环的构建。 - Suppr

Total synthesis of thiostrepton, part 1: construction of the dehydropiperidine/thiazoline-containing macrocycle.

作者信息

Nicolaou K C, Safina Brian S, Zak Mark, Estrada Anthony A, Lee Sang Hyup

机构信息

Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.

出版信息

Angew Chem Int Ed Engl. 2004 Sep 27;43(38):5087-92. doi: 10.1002/anie.200461340.

DOI:10.1002/anie.200461340

PMID:15372631

Abstract

摘要

相似文献

Total synthesis of thiostrepton, part 1: construction of the dehydropiperidine/thiazoline-containing macrocycle.

Angew Chem Int Ed Engl. 2004 Sep 27;43(38):5087-92. doi: 10.1002/anie.200461340.

Total synthesis of thiostrepton, part 2: construction of the quinaldic acid macrocycle and final stages of the synthesis.

Angew Chem Int Ed Engl. 2004 Sep 27;43(38):5092-7. doi: 10.1002/anie.200461341.

Synthetic studies on thiostrepton: construction of thiostrepton analogues with the thiazoline-containing macrocycle.

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Construction of macrocyclic thiodepsipeptides: synthesis of a nosiheptide 'southern hemisphere' model system.

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Total synthesis of thiostrepton. Retrosynthetic analysis and construction of key building blocks.

J Am Chem Soc. 2005 Aug 10;127(31):11159-75. doi: 10.1021/ja0529337.

Synthesis of chiral cyclic oligothiazolines: a novel structural motif for a macrocyclic molecule.

Chem Commun (Camb). 2006 Apr 28(16):1757-9. doi: 10.1039/b601628f. Epub 2006 Mar 15.

Stereocontrolled synthesis of the quinaldic acid macrocyclic system of thiostrepton.

Angew Chem Int Ed Engl. 2002 Jun 3;41(11):1937-40.

引用本文的文献

A brief history of antibiotics and select advances in their synthesis.

J Antibiot (Tokyo). 2018 Feb;71(2):153-184. doi: 10.1038/ja.2017.62. Epub 2017 Jul 5.

Thiopeptide antibiotics: retrospective and recent advances.

Mar Drugs. 2014 Jan 17;12(1):317-51. doi: 10.3390/md12010317.

How thiostrepton was made in the laboratory.

Angew Chem Int Ed Engl. 2012 Dec 7;51(50):12414-36. doi: 10.1002/anie.201205576. Epub 2012 Dec 3.

Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

Chem Soc Rev. 2012 Aug 7;41(15):5185-238. doi: 10.1039/c2cs35116a. Epub 2012 Jun 28.

Thiostrepton inhibits stable 70S ribosome binding and ribosome-dependent GTPase activation of elongation factor G and elongation factor 4.

Nucleic Acids Res. 2012 Jan;40(1):360-70. doi: 10.1093/nar/gkr623. Epub 2011 Sep 9.

Thiazolyl peptide antibiotic biosynthesis: a cascade of post-translational modifications on ribosomal nascent proteins.

J Biol Chem. 2010 Sep 3;285(36):27525-31. doi: 10.1074/jbc.R110.135970. Epub 2010 Jun 3.

Manipulation of thiocillin variants by prepeptide gene replacement: structure, conformation, and activity of heterocycle substitution mutants.

J Am Chem Soc. 2010 Jun 2;132(21):7519-27. doi: 10.1021/ja102339q.

Total synthesis of atrochamins F, H, I, and J through cascade reactions.

Tetrahedron. 2008 May 19;64(21):4736-4757. doi: 10.1016/j.tet.2008.02.108.

Inspirations, discoveries, and future perspectives in total synthesis.

J Org Chem. 2009 Feb 6;74(3):951-72. doi: 10.1021/jo802351b.

Recent advances in the chemistry and biology of naturally occurring antibiotics.

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Total synthesis of thiostrepton, part 1: construction of the dehydropiperidine/thiazoline-containing macrocycle.

作者信息

Nicolaou K C, Safina Brian S, Zak Mark, Estrada Anthony A, Lee Sang Hyup

机构信息

Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.

出版信息

Angew Chem Int Ed Engl. 2004 Sep 27;43(38):5087-92. doi: 10.1002/anie.200461340.

DOI:10.1002/anie.200461340

PMID:15372631

Abstract

摘要

相似文献

Total synthesis of thiostrepton, part 1: construction of the dehydropiperidine/thiazoline-containing macrocycle.

Angew Chem Int Ed Engl. 2004 Sep 27;43(38):5087-92. doi: 10.1002/anie.200461340.

Total synthesis of thiostrepton, part 2: construction of the quinaldic acid macrocycle and final stages of the synthesis.

Angew Chem Int Ed Engl. 2004 Sep 27;43(38):5092-7. doi: 10.1002/anie.200461341.

Synthetic studies on thiostrepton: construction of thiostrepton analogues with the thiazoline-containing macrocycle.

Angew Chem Int Ed Engl. 2003 Jul 28;42(29):3418-24. doi: 10.1002/anie.200351745.

A biomimetically inspired synthesis of the dehydropiperidine domain of thiostrepton.

Angew Chem Int Ed Engl. 2002 Jun 3;41(11):1941-5.

Total synthesis of thiostrepton. Assembly of key building blocks and completion of the synthesis.

J Am Chem Soc. 2005 Aug 10;127(31):11176-83. doi: 10.1021/ja052934z.

Total synthesis of (+/-)-haliclonacyclamine C.

Angew Chem Int Ed Engl. 2010 Feb 22;49(9):1599-602. doi: 10.1002/anie.200905732.

Construction of macrocyclic thiodepsipeptides: synthesis of a nosiheptide 'southern hemisphere' model system.

Chem Commun (Camb). 2008 Feb 7(5):591-3. doi: 10.1039/b715644h. Epub 2007 Nov 23.

Total synthesis of thiostrepton. Retrosynthetic analysis and construction of key building blocks.

J Am Chem Soc. 2005 Aug 10;127(31):11159-75. doi: 10.1021/ja0529337.

Synthesis of chiral cyclic oligothiazolines: a novel structural motif for a macrocyclic molecule.

Chem Commun (Camb). 2006 Apr 28(16):1757-9. doi: 10.1039/b601628f. Epub 2006 Mar 15.

Stereocontrolled synthesis of the quinaldic acid macrocyclic system of thiostrepton.

Angew Chem Int Ed Engl. 2002 Jun 3;41(11):1937-40.

引用本文的文献

A brief history of antibiotics and select advances in their synthesis.

J Antibiot (Tokyo). 2018 Feb;71(2):153-184. doi: 10.1038/ja.2017.62. Epub 2017 Jul 5.

Thiopeptide antibiotics: retrospective and recent advances.

Mar Drugs. 2014 Jan 17;12(1):317-51. doi: 10.3390/md12010317.

How thiostrepton was made in the laboratory.

Angew Chem Int Ed Engl. 2012 Dec 7;51(50):12414-36. doi: 10.1002/anie.201205576. Epub 2012 Dec 3.

Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

Chem Soc Rev. 2012 Aug 7;41(15):5185-238. doi: 10.1039/c2cs35116a. Epub 2012 Jun 28.

Thiostrepton inhibits stable 70S ribosome binding and ribosome-dependent GTPase activation of elongation factor G and elongation factor 4.

Nucleic Acids Res. 2012 Jan;40(1):360-70. doi: 10.1093/nar/gkr623. Epub 2011 Sep 9.

Thiazolyl peptide antibiotic biosynthesis: a cascade of post-translational modifications on ribosomal nascent proteins.

J Biol Chem. 2010 Sep 3;285(36):27525-31. doi: 10.1074/jbc.R110.135970. Epub 2010 Jun 3.

Manipulation of thiocillin variants by prepeptide gene replacement: structure, conformation, and activity of heterocycle substitution mutants.

J Am Chem Soc. 2010 Jun 2;132(21):7519-27. doi: 10.1021/ja102339q.

Total synthesis of atrochamins F, H, I, and J through cascade reactions.

Tetrahedron. 2008 May 19;64(21):4736-4757. doi: 10.1016/j.tet.2008.02.108.

Inspirations, discoveries, and future perspectives in total synthesis.

J Org Chem. 2009 Feb 6;74(3):951-72. doi: 10.1021/jo802351b.

Recent advances in the chemistry and biology of naturally occurring antibiotics.

Angew Chem Int Ed Engl. 2009;48(4):660-719. doi: 10.1002/anie.200801695.

Total synthesis of thiostrepton, part 1: construction of the dehydropiperidine/thiazoline-containing macrocycle.

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Total synthesis of thiostrepton, part 1: construction of the dehydropiperidine/thiazoline-containing macrocycle.

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