Second generation specific-enzyme-activated rotaxane propeptides

被引：45

作者：

Fernandes, Antony ^{[2
,3
]}

Viterisi, Aurelien ^{[2
]}

Aucagne, Vincent ^{[1
]}

Leigh, David A. ^{[2
]}

Papot, Sebastien ^{[3
]}

机构：

[1] CNRS, Ctr Biophys Mol, UPR 4301, F-45071 Orleans 2, France

[2] Univ Edinburgh, Sch Chem, Edinburgh EH9 3JJ, Midlothian, Scotland

[3] Univ Poitiers, CNRS, Lab Synth & Reactivite Subst Nat, UMR 6514, F-86022 Poitiers, France

来源：

CHEMICAL COMMUNICATIONS | 2012年 / 48卷 / 15期

基金：

英国工程与自然科学研究理事会;

关键词：

MOLECULAR MACHINE; PEPTIDE ROTAXANES; TERMINAL ALKYNES; POLYROTAXANE; DELIVERY; RELEASE; SHUTTLE; STATION; AZIDES; DNA;

D O I：

10.1039/c2cc17458h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A [2] rotaxane, in which the peptidic axle is protected from degradation by the macrocyclic sheath and terminated with a novel glycosidase-cleavable stopper, is rendered water-soluble by derivatisation with tetra(ethylene glycol) (TetEG) or glucosylated tetra(ethylene glycol) (Glc-TetEG) chains using the CuAAC 'click' reaction. The Glc-TetEG-derivatised rotaxane propeptide is > 50 000 times more soluble in aqueous media than the parent rotaxane. Activation of the water-soluble rotaxane propeptide with a beta-galactosidase efficiently releases the parent peptide.

引用

收藏

页码：2083 / 2085

页数：3

相关论文

共 35 条

[1] Phosphorus-Based Functional Groups as Hydrogen Bonding Templates for Rotaxane Formation [J].

Ahmed, Rehan ;

Altieri, Andrea ;

D'Souza, Daniel M. ;

Leigh, David A. ;

Mullen, Kathleen M. ;

Papmeyer, Marcus ;

Slawin, Alexandra M. Z. ;

Wong, Jenny K. Y. ;

Woollins, J. Derek .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (31) :12304-12310

[2] Sulfur-containing amide-based [2]rotaxanes and molecular shuttles [J].

Altieri, Andrea ;

Aucagne, Vincent ;

Carrillo, Romen ;

Clarkson, Guy J. ;

D'Souza, Daniel M. ;

Dunnett, Jennifer A. ;

Leigh, David A. ;

Mullen, Kathleen M. .

CHEMICAL SCIENCE, 2011, 2 (10) :1922-1928

[3] Switching "on" and "off" the expression of chirality in peptide rotaxanes [J].

Asakawa, M ;

Brancato, G ;

Fanti, M ;

Leigh, DA ;

Shimizu, T ;

Slawin, AMZ ;

Wong, JKY ;

Zerbetto, F ;

Zhang, SW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (12) :2939-2950

[4] Rotaxanes of cyclic peptides [J].

Aucagne, V ;

Leigh, DA ;

Lock, JS ;

Thomson, AR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (06) :1784-1785

[5] Determining the intracellular transport mechanism of a cleft-[2]rotaxane [J].

Bao, Xiaofeng ;

Isaacsohn, Idit ;

Drew, Angela F. ;

Smithrud, David B. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (37) :12229-12238

[6] Chiroptical switching in a bistable molecular shuttle [J].

Bottari, G ;

Leigh, DA ;

Pérez, EM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (44) :13360-13361

[7] From reactants to products via simple hydrogen-bonding networks: Information transmission in chemical reactions [J].

Brancato, G ;

Coutrot, F ;

Leigh, DA ;

Murphy, A ;

Wong, JKY ;

Zerbetto, F .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2002, 99 (08) :4967-4971

[8] Bistable or Oscillating State Depending on Station and Temperature in Three-Station Glycorotaxane Molecular Machines [J].

Busseron, Eric ;

Romuald, Camille ;

Coutrot, Frederic .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (33) :10062-10073

[9] A metal-complex-tolerant CuAAC 'click' protocol exemplified through the preparation of homo- and mixed-metal-coordinated [2]rotaxanes [J].

Cabrera, Diego Gonzalez ;

Koivisto, Bryan D. ;

Leigh, David A. .

CHEMICAL COMMUNICATIONS, 2007, (41) :4218-4220

[10] Enzymatic synthesis and photoswitchable enzymatic cleavage of a peptide-linked rotaxane [J].

Cheetham, AG ;

Hutchings, MG ;

Claridge, TDW ;

Anderson, HL .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (10) :1596-1599

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