Literature DB >> 18783225

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

Xuechen Li1, Yu Yuan, Cindy Kan, Samuel J Danishefsky.   

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.

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Year:  2008        PMID: 18783225      PMCID: PMC2580816          DOI: 10.1021/ja804709s

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  13 in total

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Review 3.  Synthetic preparation of N-methyl-alpha-amino acids.

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4.  Reaction of isonitriles with carboxylic acids in a cavitand: observation of elusive isoimide intermediates.

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5.  Mechanistic studies of peptide oxazolone racemization.

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Journal:  Tetrahedron       Date:  1967-05       Impact factor: 2.457

6.  Synthesis of peptide oxazolones and related compounds.

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Journal:  Tetrahedron       Date:  1967-05       Impact factor: 2.457

7.  Reaction of essentially free benzyl cations with acetonitrile; synthesis of ethanimidic carboxylic anhydrides and unsymmetrical diacylamines

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Journal:  J Org Chem       Date:  2000-02-25       Impact factor: 4.354

8.  The coupling of isonitriles and carboxylic acids occurring by sequential concerted rearrangement mechanisms.

Authors:  Gavin O Jones; Xuechen Li; Amy E Hayden; K N Houk; Samuel J Danishefsky
Journal:  Org Lett       Date:  2008-08-16       Impact factor: 6.005

9.  Reaction of carboxylic acids and isonitriles in small spaces.

Authors:  Jun-Li Hou; Dariush Ajami; Julius Rebek
Journal:  J Am Chem Soc       Date:  2008-05-29       Impact factor: 15.419

10.  Ribosomal synthesis of N-methyl peptides.

Authors:  Alexander O Subtelny; Matthew C T Hartman; Jack W Szostak
Journal:  J Am Chem Soc       Date:  2008-04-11       Impact factor: 15.419

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  20 in total

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Authors:  Xiangyang Wu; Jennifer L Stockdill; Peter K Park; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2012-01-17       Impact factor: 15.419

2.  Control of Nanospaces with Molecular Devices.

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4.  Encouraging progress in the ω-aspartylation of complex oligosaccharides as a general route to β-N-linked glycopolypeptides.

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5.  On the Preparation of Enantiomerically Pure Isonitriles from Amino Acid Esters and Peptides.

Authors:  Jianglong Zhu; Xiangyang Wu; Samuel J Danishefsky
Journal:  Tetrahedron Lett       Date:  2009-02-04       Impact factor: 2.415

6.  Enhancing the scope of the Diels-Alder reaction through isonitrile chemistry: emergence of a new class of acyl-activated dienophiles.

Authors:  Steven D Townsend; Xiangyang Wu; Samuel J Danishefsky
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7.  Solid-phase peptide synthesis and solid-phase fragment coupling mediated by isonitriles.

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8.  Reaction of thioacids with isocyanates and isothiocyanates: a convenient amide ligation process.

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9.  Thio FCMA intermediates as strong acyl donors: a general solution to the formation of complex amide bonds.

Authors:  Yu Rao; Xuechen Li; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2009-09-16       Impact factor: 15.419

10.  Revisiting oxytocin through the medium of isonitriles.

Authors:  Ting Wang; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2012-08-02       Impact factor: 15.419

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