Literature DB >> 30095837

Tuning of protease resistance in oligopeptides through N-alkylation.

Revital Kaminker1, Athina Anastasaki, Will R Gutekunst, Yingdong Luo, Sang-Ho Lee, Craig J Hawker.   

Abstract

N-Methylation of amino acids is an effective way to create protease resistance in both natural and synthetic peptides. However, alkyl substituents other than N-methyl have not been extensively studied. Here, we prepare and examine a series of N-substituted peptides in which the size and length of the alkyl group is modulated. These design insights provide a unique and modular handle for tuning proteolysis in oligopeptides.

Entities:  

Year:  2018        PMID： 30095837      PMCID： PMC6141190          DOI： 10.1039/c8cc04407d

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  28 in total

Review 1.  The road to the synthesis of "difficult peptides".

Authors:  Marta Paradís-Bas; Judit Tulla-Puche; Fernando Albericio
Journal:  Chem Soc Rev       Date:  2015-11-27       Impact factor: 54.564

Review 2.  Peptide therapeutics: current status and future directions.

Authors:  Keld Fosgerau; Torsten Hoffmann
Journal:  Drug Discov Today       Date:  2014-10-17       Impact factor: 7.851

3.  Intrinsic backbone preferences are fully present in blocked amino acids.

Authors:  Franc Avbelj; Simona Golic Grdadolnik; Joze Grdadolnik; Robert L Baldwin
Journal:  Proc Natl Acad Sci U S A       Date:  2006-01-19       Impact factor: 11.205

4.  Solid-phase synthesis of diverse peptide tertiary amides by reductive amination.

Authors:  Kevin Pels; Thomas Kodadek
Journal:  ACS Comb Sci       Date:  2015-02-25       Impact factor: 3.784

5.  Dioxin-binding pentapeptide for use in a high-sensitivity on-bead detection assay.

Authors:  Chikashi Nakamura; Yasuhiro Inuyama; Hiroki Goto; Ikuo Obataya; Nao Kaneko; Noriyuki Nakamura; Noriaki Santo; Jun Miyake
Journal:  Anal Chem       Date:  2005-12-01       Impact factor: 6.986

6.  Sequence-specific polypeptoids: a diverse family of heteropolymers with stable secondary structure.

Authors:  K Kirshenbaum; A E Barron; R A Goldsmith; P Armand; E K Bradley; K T Truong; K A Dill; F E Cohen; R N Zuckermann
Journal:  Proc Natl Acad Sci U S A       Date:  1998-04-14       Impact factor: 11.205

7.  Kinetics and equilibria of cis/trans isomerization of backbone amide bonds in peptoids.

Authors:  Qiang Sui; Dan Borchardt; Dallas L Rabenstein
Journal:  J Am Chem Soc       Date:  2007-09-07       Impact factor: 15.419

8.  Computational and experimental analysis of short peptide motifs for enzyme inhibition.

Authors:  Jinglin Fu; Luca Larini; Anthony J Cooper; John W Whittaker; Azka Ahmed; Junhao Dong; Minyoung Lee; Ting Zhang
Journal:  PLoS One       Date:  2017-08-15       Impact factor: 3.240

9.  Short peptides self-assemble to produce catalytic amyloids.

Authors:  Caroline M Rufo; Yurii S Moroz; Olesia V Moroz; Jan Stöhr; Tyler A Smith; Xiaozhen Hu; William F DeGrado; Ivan V Korendovych
Journal:  Nat Chem       Date:  2014-03-16       Impact factor: 24.427

Review 10.  The alphabet of intrinsic disorder: I. Act like a Pro: On the abundance and roles of proline residues in intrinsically disordered proteins.

Authors:  Francois-Xavier Theillet; Lajos Kalmar; Peter Tompa; Kyou-Hoon Han; Philipp Selenko; A Keith Dunker; Gary W Daughdrill; Vladimir N Uversky
Journal:  Intrinsically Disord Proteins       Date:  2013-04-01
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  1 in total

1.  Structure-Property Relationship Study of N-(Hydroxy)Peptides for the Design of Self-Assembled Parallel β-Sheets.

Authors:  Alexis D Richaud; Stéphane P Roche
Journal:  J Org Chem       Date:  2020-09-17       Impact factor: 4.354
  1 in total

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