短肽中螺旋含量的光控
Photo-control of helix content in a short peptide.
作者信息
Kumita J R, Smart O S, Woolley G A
机构信息
Department of Chemistry, University of Toronto, 80 Saint George Street, Toronto M5S 3H6, Canada.
出版信息
Proc Natl Acad Sci U S A. 2000 Apr 11;97(8):3803-8. doi: 10.1073/pnas.97.8.3803.
Abstract
The alpha-helix is a key structural element in a wide range of peptides and proteins. We report here the design, synthesis, and characterization of a modified peptide in which the helix content can be reversibly photoregulated. The peptide contains two cysteine residues that are cross-linked by an azobenzene derivative in an intramolecular fashion. In accordance with the design, the photoisomerization of the azobenzene cross-linker from the trans to the cis form causes a large increase in the helix content of the peptide, in water.
摘要
α-螺旋是多种肽和蛋白质中的关键结构元件。我们在此报告一种修饰肽的设计、合成及表征，其螺旋含量可通过光进行可逆调节。该肽含有两个半胱氨酸残基，它们通过分子内的偶氮苯衍生物交联。按照设计，偶氮苯交联剂从反式到顺式的光异构化导致该肽在水中的螺旋含量大幅增加。
相似文献
1
Photo-control of helix content in a short peptide.
Proc Natl Acad Sci U S A. 2000 Apr 11;97(8):3803-8. doi: 10.1073/pnas.97.8.3803.
2
Photo-control of peptide conformation on a timescale of seconds with a conformationally constrained, blue-absorbing, photo-switchable linker.
Org Biomol Chem. 2008 Dec 7;6(23):4323-32. doi: 10.1039/b810533b. Epub 2008 Sep 24.
3
Synthesis and characterization of a long, rigid photoswitchable cross-linker for promoting peptide and protein conformational change.
Chembiochem. 2008 Sep 1;9(13):2147-54. doi: 10.1002/cbic.200800196.
4
Photo-control of peptide helix content by an azobenzene cross-linker: steric interactions with underlying residues are not critical.
Protein Eng. 2002 Jul;15(7):561-9. doi: 10.1093/protein/15.7.561.
5
A blue-green absorbing cross-linker for rapid photoswitching of peptide helix content.
Bioconjug Chem. 2006 May-Jun;17(3):670-6. doi: 10.1021/bc050363u.
6
Origins of helix-coil switching in a light-sensitive peptide.
Biochemistry. 2004 Dec 14;43(49):15329-38. doi: 10.1021/bi048152k.
7
A water-soluble azobenzene cross-linker for photocontrol of peptide conformation.
Bioconjug Chem. 2003 Jul-Aug;14(4):824-9. doi: 10.1021/bc0340161.
8
Using an azobenzene cross-linker to either increase or decrease peptide helix content upon trans-to-cis photoisomerization.
Chem Biol. 2002 Mar;9(3):391-7. doi: 10.1016/s1074-5521(02)00109-6.
9
Photocontrol of the collagen triple helix: synthesis and conformational characterization of bis-cysteinyl collagenous peptides with an azobenzene clamp.
Chemistry. 2007;13(10):2966-73. doi: 10.1002/chem.200601162.
10
Aromatic side-chain contribution to far-ultraviolet circular dichroism of helical peptides and its effect on measurement of helix propensities.
Biochemistry. 1993 Jun 1;32(21):5560-5. doi: 10.1021/bi00072a010.
引用本文的文献
1
Effects of binding partners on thermal reversion rates of photoswitchable molecules.
Proc Natl Acad Sci U S A. 2025 Mar 11;122(10):e2414748122. doi: 10.1073/pnas.2414748122. Epub 2025 Mar 4.
2
Recent Advances in Metal-Free Peptide Stapling Strategies.
Chem Bio Eng. 2024 Jun 11;1(7):593-605. doi: 10.1021/cbe.3c00123. eCollection 2024 Aug 22.
3
Red-light modulated -chloro azobenzene photoswitch for peptide stapling aromatic substitution.
RSC Chem Biol. 2023 Oct 19;5(1):49-54. doi: 10.1039/d3cb00176h. eCollection 2024 Jan 3.
4
Helicase Activity Modulation with On-Demand Light-Based Conformational Control.
J Am Chem Soc. 2023 Oct 4;145(39):21253-21262. doi: 10.1021/jacs.3c05254. Epub 2023 Sep 22.
5
Using azobenzene photocontrol to set proteins in motion.
Nat Rev Chem. 2022 Feb;6(2):112-124. doi: 10.1038/s41570-021-00338-6. Epub 2021 Dec 7.
6
Rational design of stapled antimicrobial peptides.
Amino Acids. 2023 Apr;55(4):421-442. doi: 10.1007/s00726-023-03245-w. Epub 2023 Feb 12.
7
Azobenzene-Based Amino Acids for the Photocontrol of Coiled-Coil Peptides.
Bioconjug Chem. 2023 Feb 15;34(2):345-357. doi: 10.1021/acs.bioconjchem.2c00534. Epub 2023 Jan 27.
8
Photochemical control of drug efficacy - a comparison of uncaging and photoswitching ifenprodil on NMDA receptors.
ChemPhotoChem. 2021 May;5(5):445-454. doi: 10.1002/cptc.202000240. Epub 2021 Feb 4.
9
Structural guidelines for stabilization of α-helical coiled coils PEG stapling.
RSC Chem Biol. 2022 Jul 26;3(9):1096-1104. doi: 10.1039/d1cb00237f. eCollection 2022 Aug 31.
10
Tuning of Peptide Cytotoxicity with Cell Penetrating Motif Activatable by Matrix Metalloproteinase-2.
ACS Omega. 2022 Aug 16;7(34):29684-29691. doi: 10.1021/acsomega.2c02127. eCollection 2022 Aug 30.
本文引用的文献
1
Large Circular Dichroism Ellipticities for N-Templated Helical Polypeptides Are Inconsistent with Currently Accepted Helicity Algorithms.
Angew Chem Int Ed Engl. 1999 May 3;38(9):1290-1292. doi: 10.1002/(SICI)1521-3773(19990503)38:9<1290::AID-ANIE1290>3.0.CO;2-E.
2
The structure of proteins; two hydrogen-bonded helical configurations of the polypeptide chain.
Proc Natl Acad Sci U S A. 1951 Apr;37(4):205-11. doi: 10.1073/pnas.37.4.205.
3
Photomodulation of the Conformation of Cyclic Peptides with Azobenzene Moieties in the Peptide Backbone.
Angew Chem Int Ed Engl. 1999 Sep;38(18):2771-2774. doi: 10.1002/(sici)1521-3773(19990917)38:18<2771::aid-anie2771>3.0.co;2-w.
4
Design and semisynthesis of spermine-sensitive Ribonuclease S'.
Bioorg Med Chem Lett. 1999 May 3;9(9):1215-8. doi: 10.1016/s0960-894x(99)00189-4.
5
Stereochemical control of peptide folding.
Bioorg Med Chem. 1999 Jan;7(1):105-17. doi: 10.1016/s0968-0896(98)00221-1.
6
Alanine is helix-stabilizing in both template-nucleated and standard peptide helices.
Proc Natl Acad Sci U S A. 1999 Mar 30;96(7):3682-7. doi: 10.1073/pnas.96.7.3682.
7
Fast events in protein folding: the time evolution of primary processes.
Annu Rev Phys Chem. 1998;49:173-202. doi: 10.1146/annurev.physchem.49.1.173.
8
Conformational consequences of i, i + 3 cystine linkages: nucleation for alpha-helicity?
J Pept Res. 1997 May;49(5):404-14. doi: 10.1111/j.1399-3011.1997.tb00892.x.
9
Conformational switching in designed peptides: the helix/sheet transition.
Fold Des. 1996;1(2):91-101. doi: 10.1016/S1359-0278(96)00018-1.
10
Methods to estimate the conformation of proteins and polypeptides from circular dichroism data.
Anal Biochem. 1996 Mar 1;235(1):1-10. doi: 10.1006/abio.1996.0084.
Zotero 插件