Literature DB >> 18083557

Protected aminooxyprolines for expedited library synthesis: application to Tsg101-directed proline-oxime containing peptides.

Fa Liu1, Andrew G Stephen, Robert J Fisher, Terrence R Burke.   

Abstract

The stereoselective synthesis of aminooxy-containing proline analogues bearing Fmoc/Boc or Fmoc/Mtt protection that renders them suitable for incorporation into peptides using Fmoc protocols is reported. Acid-catalyzed unmasking at the completion of peptide synthesis yields free aminooxy-functionalities for oxime formation through reaction with libraries of aldehydes. This allows post solid-phase diversification strategies that may facilitate structure-activity relationship studies.

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Year:  2007        PMID： 18083557      PMCID： PMC2488393          DOI： 10.1016/j.bmcl.2007.12.003

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  16 in total

Review 1.  Recognition of proline-rich motifs by protein-protein-interaction domains.

Authors:  Linda J Ball; Ronald Kühne; Jens Schneider-Mergener; Hartmut Oschkinat
Journal:  Angew Chem Int Ed Engl       Date:  2005-05-06       Impact factor: 15.336

2.  Convergent synthesis of a complex oxime library using chemical domain shuffling.

Authors:  Shun Su; Dayle E Acquilano; Jeevanandam Arumugasamy; Aaron B Beeler; Erin L Eastwood; Joshua R Giguere; Ping Lan; Xiaoguang Lei; Geanna K Min; Adam R Yeager; Ya Zhou; James S Panek; John K Snyder; Scott E Schaus; John A Porco
Journal:  Org Lett       Date:  2005-06-23       Impact factor: 6.005

Review 3.  Naturally occurring proline analogues.

Authors:  A B Mauger
Journal:  J Nat Prod       Date:  1996-12       Impact factor: 4.050

4.  Mild and selective sodium azide mediated cleavage of p-nitrobenzoic esters.

Authors:  J A Gómez-Vidal; M T Forrester; R B Silverman
Journal:  Org Lett       Date:  2001-08-09       Impact factor: 6.005

Review 5.  Retrovirus budding.

Authors:  Dimiter G Demirov; Eric O Freed
Journal:  Virus Res       Date:  2004-12       Impact factor: 3.303

6.  The impact of pyrrolidine hydroxylation on the conformation of proline-containing peptides.

Authors:  Carol M Taylor; Renaud Hardré; Patrick J B Edwards
Journal:  J Org Chem       Date:  2005-02-18       Impact factor: 4.354

7.  Versatile and efficient synthesis of protein-polysaccharide conjugate vaccines using aminooxy reagents and oxime chemistry.

Authors:  Andrew Lees; Goutam Sen; Alberto LopezAcosta
Journal:  Vaccine       Date:  2005-09-12       Impact factor: 3.641

8.  Bisaryloxime ethers as potent inhibitors of transthyretin amyloid fibril formation.

Authors:  Steven M Johnson; H Michael Petrassi; Satheesh K Palaninathan; Nilofar N Mohamedmohaideen; Hans E Purkey; Christopher Nichols; Kyle P Chiang; Traci Walkup; James C Sacchettini; K Barry Sharpless; Jeffery W Kelly
Journal:  J Med Chem       Date:  2005-03-10       Impact factor: 7.446

9.  Side-chain effects on peptidyl-prolyl cis/trans isomerisation.

Authors:  U Reimer; G Scherer; M Drewello; S Kruber; M Schutkowski; G Fischer
Journal:  J Mol Biol       Date:  1998-06-05       Impact factor: 5.469

Review 10.  Proline motifs in peptides and their biological processing.

Authors:  G Vanhoof; F Goossens; I De Meester; D Hendriks; S Scharpé
Journal:  FASEB J       Date:  1995-06       Impact factor: 5.191
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  10 in total

1.  Synthesis of a Homologous Series of Side Chain Extended Orthogonally-Protected Aminooxy-Containing Amino Acids.

Authors:  Fa Liu; Joshua Thomas; Terrence R Burke
Journal:  Synthesis (Stuttg)       Date:  2008       Impact factor: 3.157

2.  Oxime-based linker libraries as a general approach for the rapid generation and screening of multidentate inhibitors.

Authors:  Medhanit Bahta; Fa Liu; Sung-Eun Kim; Andrew G Stephen; Robert J Fisher; Terrence R Burke
Journal:  Nat Protoc       Date:  2012-03-15       Impact factor: 13.491

3.  Utilization of nitrophenylphosphates and oxime-based ligation for the development of nanomolar affinity inhibitors of the Yersinia pestis outer protein H (YopH) phosphatase.

Authors:  Medhanit Bahta; George T Lountos; Beverly Dyas; Sung-Eun Kim; Robert G Ulrich; David S Waugh; Terrence R Burke
Journal:  J Med Chem       Date:  2011-03-28       Impact factor: 7.446

4.  Elucidation of New Binding Interactions with the Tumor Susceptibility Gene 101 (Tsg101) Protein Using Modified HIV-1 Gag-p6 Derived Peptide Ligands.

Authors:  Sung-Eun Kim; Fa Liu; Young Jun Im; Andrew G Stephen; Matthew J Fivash; Abdul A Waheed; Eric O Freed; Robert J Fisher; James H Hurley; Terrence R Burke
Journal:  ACS Med Chem Lett       Date:  2011-05-12       Impact factor: 4.345

5.  Identification of high affinity polo-like kinase 1 (Plk1) polo-box domain binding peptides using oxime-based diversification.

Authors:  Fa Liu; Jung-Eun Park; Wen-Jian Qian; Dan Lim; Andrej Scharow; Thorsten Berg; Michael B Yaffe; Kyung S Lee; Terrence R Burke
Journal:  ACS Chem Biol       Date:  2012-02-14       Impact factor: 5.100

Review 6.  Updating on Roles of HIV Intrinsic Factors: A Review of Their Antiviral Mechanisms and Emerging Functions.

Authors:  Sudarat Hadpech; Sutpirat Moonmuang; Koollawat Chupradit; Umpa Yasamut; Chatchai Tayapiwatana
Journal:  Intervirology       Date:  2021-08-31       Impact factor: 2.294

7.  Proline editing: a general and practical approach to the synthesis of functionally and structurally diverse peptides. Analysis of steric versus stereoelectronic effects of 4-substituted prolines on conformation within peptides.

Authors:  Anil K Pandey; Devan Naduthambi; Krista M Thomas; Neal J Zondlo
Journal:  J Am Chem Soc       Date:  2013-03-11       Impact factor: 15.419

8.  SAR by oxime-containing peptide libraries: application to Tsg101 ligand optimization.

Authors:  Fa Liu; Andrew G Stephen; Abdul A Waheed; M Javad Aman; Eric O Freed; Robert J Fisher; Terrence R Burke
Journal:  Chembiochem       Date:  2008-08-11       Impact factor: 3.164

9.  Application of ring-closing metathesis macrocyclization to the development of Tsg101-binding antagonists.

Authors:  Fa Liu; Andrew G Stephen; Abdul A Waheed; Eric O Freed; Robert J Fisher; Terrence R Burke
Journal:  Bioorg Med Chem Lett       Date:  2009-10-29       Impact factor: 2.823

Review 10.  Application of Post Solid-Phase Oxime Ligation to Fine-Tune Peptide-Protein Interactions.

Authors:  Xue Zhi Zhao; Fa Liu; Terrence R Burke
Journal:  Molecules       Date:  2020-06-18       Impact factor: 4.411
  10 in total

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