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Literature DB >> 22368033

A fascinating journey into history: exploration of the world of isonitriles en route to complex amides.

Rebecca M Wilson¹, Jennifer L Stockdill, Xiangyang Wu, Xuechen Li, Paul A Vadola, Peter K Park, Ping Wang, Samuel J Danishefsky.

Abstract

We describe herein our recent explorations in the field of isonitrile chemistry. An array of broadly useful coupling methodologies has been developed for the formation of peptidyl and glycopeptidyl amide bonds. We further describe the application of these methods to the syntheses of complex systems, including the cyclic peptide cyclosporine A, constrained peptide systems, and heterocycles.

Entities: Chemical Disease Gene Species

Mesh：

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Year: 2012 PMID： 22368033 PMCID： PMC3409437 DOI： 10.1002/anie.201106628

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

34 in total

1. A xanthocillin-like alkaloid from the insect pathogenic fungus Cordyceps brunnearubra BCC 1395.

Authors: Masahiko Isaka; Bundit Boonkhao; Pranee Rachtawee; Patchanee Auncharoen
Journal: J Nat Prod Date: 2007-02-01 Impact factor: 4.050

Review 2. Glycoprotein synthesis: an update.

Authors: David P Gamblin; Eoin M Scanlan; Benjamin G Davis
Journal: Chem Rev Date: 2009-01 Impact factor: 60.622

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

Authors: Per Restorp; Julius Rebek
Journal: J Am Chem Soc Date: 2008-08-13 Impact factor: 15.419

Review 4. The medicinal chemistry of peptides.

Authors: J J Nestor
Journal: Curr Med Chem Date: 2009 Impact factor: 4.530

5. [Cyclosporin A, a Peptide Metabolite from Trichoderma polysporum (Link ex Pers.) Rifai, with a remarkable immunosuppressive activity].

Authors: A Rüegger; M Kuhn; H Lichti; H R Loosli; R Huguenin; C Quiquerez; A von Wartburg
Journal: Helv Chim Acta Date: 1976 Impact factor: 2.164

6. 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

7. On the synthesis of conformationally modified peptides through isonitrile chemistry: implications for dealing with polypeptide aggregation.

Authors: Xiangyang Wu; Peter K Park; Samuel J Danishefsky
Journal: J Am Chem Soc Date: 2011-05-03 Impact factor: 15.419

8. Thio-mediated synthesis of derivatized N-linked glycopeptides using isonitrile chemistry.

Authors: Xiangyang Wu; Yu Yuan; Xuechen Li; Samuel J Danishefsky
Journal: Tetrahedron Lett Date: 2009-08-12 Impact factor: 2.415

9. Recent Departures in the Synthesis of Peptides and Glycopeptides.

Authors: Cindy Kan; Samuel J Danishefsky
Journal: Tetrahedron Date: 2009-11-07 Impact factor: 2.457

10. Side reactions in peptide synthesis. VII. Sequence dependence in the formation of aminosuccinyl derivatives from beta-benzyl-aspartyl peptides.

Authors: M Bodanszky; J Z Kwei
Journal: Int J Pept Protein Res Date: 1978-08

14 in total

1. Total Chemical Synthesis and Folding of All-l and All-d Variants of Oncogenic KRas(G12V).

Authors: Adam M Levinson; John H McGee; Andrew G Roberts; Gardner S Creech; Ting Wang; Michael T Peterson; Ronald C Hendrickson; Gregory L Verdine; Samuel J Danishefsky
Journal: J Am Chem Soc Date: 2017-05-22 Impact factor: 15.419

2. Efficient isocyanide-less isocyanide-based multicomponent reactions.

Authors: Constantinos G Neochoritis; Silvia Stotani; Bhupendra Mishra; Alexander Dömling
Journal: Org Lett Date: 2015-03-31 Impact factor: 6.005

3. Engineering of therapeutic polypeptides through chemical synthesis: early lessons from human parathyroid hormone and analogues.

Authors: Suwei Dong; Shiying Shang; Jianfeng Li; Zhongping Tan; Thomas Dean; Akira Maeda; Thomas J Gardella; Samuel J Danishefsky
Journal: J Am Chem Soc Date: 2012-08-29 Impact factor: 15.419

4. Solid-phase peptide synthesis and solid-phase fragment coupling mediated by isonitriles.

Authors: Ting Wang; Samuel J Danishefsky
Journal: Proc Natl Acad Sci U S A Date: 2013-07-02 Impact factor: 11.205

5. Fully Synthetic Granulocyte Colony-Stimulating Factor Enabled by Isonitrile-Mediated Coupling of Large, Side-Chain-Unprotected Peptides.

Authors: Andrew G Roberts; Eric V Johnston; Jae-Hung Shieh; Joseph P Sondey; Ronald C Hendrickson; Malcolm A S Moore; Samuel J Danishefsky
Journal: J Am Chem Soc Date: 2015-10-01 Impact factor: 15.419

6. An advance in the chemical synthesis of homogeneous N-linked glycopolypeptides by convergent aspartylation.

Authors: Ping Wang; Baptiste Aussedat; Yusufbhai Vohra; Samuel J Danishefsky
Journal: Angew Chem Int Ed Engl Date: 2012-09-25 Impact factor: 15.336

Review 7. Syntheses and biological studies of marine terpenoids derived from inorganic cyanide.

Authors: Martin J Schnermann; Ryan A Shenvi
Journal: Nat Prod Rep Date: 2015-04 Impact factor: 13.423

8. Deciphering the Reaction Pathway of Mononuclear Iron Enzyme-Catalyzed N≡C Triple Bond Formation in Isocyanide Lipopeptide and Polyketide Biosynthesis.

Authors: Tzu-Yu Chen; Ziyang Zheng; Xuan Zhang; Jinfeng Chen; Lide Cha; Yijie Tang; Yisong Guo; Jiahai Zhou; Binju Wang; Hung-Wen Liu; Wei-Chen Chang
Journal: ACS Catal Date: 2022-01-31 Impact factor: 13.700

9. 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

Review 10. Getting in shape: controlling peptide bioactivity and bioavailability using conformational constraints.

Authors: Jonathan E Bock; Jason Gavenonis; Joshua A Kritzer
Journal: ACS Chem Biol Date: 2012-11-30 Impact factor: 5.100