Suppr超能文献

探讨异腈与羧酸偶联中的机理问题:形成肽类结构的潜在途径。

Addressing mechanistic issues in the coupling of isonitriles and carboxylic acids: potential routes to peptidic constructs.

作者信息

Li Xuechen, Yuan Yu, Kan Cindy, Danishefsky Samuel J

机构信息

Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, New York 10065, USA.

出版信息

J Am Chem Soc. 2008 Oct 8;130(40):13225-7. doi: 10.1021/ja804709s. Epub 2008 Sep 11.

Abstract

Mechanistic issues surrounding the two component coupling (2CC) reaction of carboxylic acids with isonitriles have been investigated. Experimental details suggest the formimidate carboxylate mixed anhydride intermediate exists in both interdictable and noninterdictable form. Furthermore, the 2CC reaction has been applied to the synthesis of a tripeptide featuring two formyl functional groups.

摘要

围绕羧酸与异腈的双组分偶联(2CC)反应的机理问题已得到研究。实验细节表明,甲脒基羧酸酯混合酸酐中间体以可阻断和不可阻断两种形式存在。此外,2CC反应已应用于合成具有两个甲酰基官能团的三肽。

相似文献

1
Addressing mechanistic issues in the coupling of isonitriles and carboxylic acids: potential routes to peptidic constructs.
J Am Chem Soc. 2008 Oct 8;130(40):13225-7. doi: 10.1021/ja804709s. Epub 2008 Sep 11.
3
The coupling of isonitriles and carboxylic acids occurring by sequential concerted rearrangement mechanisms.
Org Lett. 2008 Sep 18;10(18):4093-6. doi: 10.1021/ol8016287. Epub 2008 Aug 16.
4
Noncatalytic reaction of isonitriles and carboxylic acids en route to amide-type linkages.
Nat Protoc. 2008;3(10):1666-70. doi: 10.1038/nprot.2008.153.
5
Reaction of isonitriles with carboxylic acids in a cavitand: observation of elusive isoimide intermediates.
J Am Chem Soc. 2008 Sep 10;130(36):11850-1. doi: 10.1021/ja803854r. Epub 2008 Aug 13.
6
7
Solid-phase peptide synthesis and solid-phase fragment coupling mediated by isonitriles.
Proc Natl Acad Sci U S A. 2013 Jul 16;110(29):11708-13. doi: 10.1073/pnas.1310431110. Epub 2013 Jul 2.
8
Reaction of carboxylic acids and isonitriles in small spaces.
J Am Chem Soc. 2008 Jun 25;130(25):7810-1. doi: 10.1021/ja802288k. Epub 2008 May 29.
9
TBHP-promoted sequential carboxamidation and aromatisation of aryl isonitriles with formamides.
Org Biomol Chem. 2014 Dec 7;12(45):9257-63. doi: 10.1039/c4ob01850h.

引用本文的文献

1
General Approach to Amides through Decarboxylative Radical Cross-Coupling of Carboxylic Acids and Isocyanides.
Org Lett. 2024 Apr 26;26(16):3380-3385. doi: 10.1021/acs.orglett.4c00872. Epub 2024 Apr 12.
2
6-Halo-2-pyridone as an efficient organocatalyst for ester aminolysis.
RSC Adv. 2021 Jul 14;11(40):24588-24593. doi: 10.1039/d1ra04651a. eCollection 2021 Jul 13.
3
Artificial bioconjugates with naturally occurring linkages: the use of phosphodiester.
Beilstein J Org Chem. 2018 Jul 27;14:1946-1955. doi: 10.3762/bjoc.14.169. eCollection 2018.
4
Solid-phase peptide synthesis and solid-phase fragment coupling mediated by isonitriles.
Proc Natl Acad Sci U S A. 2013 Jul 16;110(29):11708-13. doi: 10.1073/pnas.1310431110. Epub 2013 Jul 2.
5
Revisiting oxytocin through the medium of isonitriles.
J Am Chem Soc. 2012 Aug 15;134(32):13244-7. doi: 10.1021/ja3063452. Epub 2012 Aug 2.
7
A fascinating journey into history: exploration of the world of isonitriles en route to complex amides.
Angew Chem Int Ed Engl. 2012 Mar 19;51(12):2834-48. doi: 10.1002/anie.201106628. Epub 2012 Feb 24.
9
Rhodium-catalyzed annulation of N-benzoylsulfonamide with isocyanide through C-H activation.
Chemistry. 2011 Nov 4;17(45):12591-5. doi: 10.1002/chem.201102475. Epub 2011 Oct 4.
10
On the Preparation of Enantiomerically Pure Isonitriles from Amino Acid Esters and Peptides.
Tetrahedron Lett. 2009 Feb 4;50(5):577-579. doi: 10.1016/j.tetlet.2008.11.069.

本文引用的文献

1
The coupling of isonitriles and carboxylic acids occurring by sequential concerted rearrangement mechanisms.
Org Lett. 2008 Sep 18;10(18):4093-6. doi: 10.1021/ol8016287. Epub 2008 Aug 16.
2
Reaction of isonitriles with carboxylic acids in a cavitand: observation of elusive isoimide intermediates.
J Am Chem Soc. 2008 Sep 10;130(36):11850-1. doi: 10.1021/ja803854r. Epub 2008 Aug 13.
3
Reaction of carboxylic acids and isonitriles in small spaces.
J Am Chem Soc. 2008 Jun 25;130(25):7810-1. doi: 10.1021/ja802288k. Epub 2008 May 29.
4
Ribosomal synthesis of N-methyl peptides.
J Am Chem Soc. 2008 May 14;130(19):6131-6. doi: 10.1021/ja710016v. Epub 2008 Apr 11.
5
8
Synthetic preparation of N-methyl-alpha-amino acids.
Chem Rev. 2004 Dec;104(12):5823-46. doi: 10.1021/cr030024z.
9
N- and Calpha-methylation in biologically active peptides: synthesis, structural and functional aspects.
Curr Med Chem. 2004 Nov;11(21):2799-822. doi: 10.2174/0929867043364108.
10
Multicomponent Reactions with Isocyanides.
Angew Chem Int Ed Engl. 2000 Sep 15;39(18):3168-3210. doi: 10.1002/1521-3773(20000915)39:18<3168::aid-anie3168>3.0.co;2-u.

文献AI研究员

20分钟写一篇综述,助力文献阅读效率提升50倍。

立即体验

用中文搜PubMed

大模型驱动的PubMed中文搜索引擎

马上搜索

文档翻译

学术文献翻译模型,支持多种主流文档格式。

立即体验