蛋白质设计与生物自组装的新范式
A New Paradigm for Protein Design and Biological Self-Assembly.
作者信息
Akçay Gizem, Kumar Krishna
机构信息
Department of Chemistry, Tufts University, Medford, MA 02155.
出版信息
J Fluor Chem. 2009 Dec 1;130(12):1178-1182. doi: 10.1016/j.jfluchem.2009.09.002.
Abstract
Very few molecules with biological origins contain the element fluorine. Nature's inability to incorporate fluorine into biomolecules is related to the low concentration of free fluoride in sea and surface water. However, judicious introduction of fluorine into proteins, nucleic acids, lipids and carbohydrates has allowed mechanistic scrutiny of enzyme catalysis, control of protein oligomerization in membranes, clustered display of ligands on surfaces of living cells, and in increasing the protease stability of protein and peptide therapeutics.
摘要
具有生物来源的分子中含氟的极少。自然界无法将氟纳入生物分子与海水中和地表水中游离氟的低浓度有关。然而，将氟明智地引入蛋白质、核酸、脂质和碳水化合物中，有助于对酶催化进行机理研究、控制膜中蛋白质的寡聚化、在活细胞表面成簇展示配体，以及提高蛋白质和肽类治疗药物的蛋白酶稳定性。
相似文献
1
A New Paradigm for Protein Design and Biological Self-Assembly.
J Fluor Chem. 2009 Dec 1;130(12):1178-1182. doi: 10.1016/j.jfluchem.2009.09.002.
2
Planning Implications Related to Sterilization-Sensitive Science Investigations Associated with Mars Sample Return (MSR).
Astrobiology. 2022 Jun;22(S1):S112-S164. doi: 10.1089/AST.2021.0113. Epub 2022 May 19.
3
Deciphering the Fluorine Code-The Many Hats Fluorine Wears in a Protein Environment.
Acc Chem Res. 2017 Sep 19;50(9):2093-2103. doi: 10.1021/acs.accounts.7b00226. Epub 2017 Aug 12.
4
Tailoring of Peptide Vesicles: A Bottom-Up Chemical Approach.
Acc Chem Res. 2021 Apr 20;54(8):1934-1949. doi: 10.1021/acs.accounts.0c00690. Epub 2021 Apr 6.
5
Continual reproduction of self-assembling oligotriazole peptide nanomaterials.
Nat Commun. 2017 Sep 28;8(1):730. doi: 10.1038/s41467-017-00849-1.
6
Carbohydrates in peptide and protein design.
Biopolymers. 2005;80(6):747-61. doi: 10.1002/bip.20300.
7
Metal-directed protein self-assembly.
Acc Chem Res. 2010 May 18;43(5):661-72. doi: 10.1021/ar900273t.
8
Establishing Fluorine-Containing Amino Acids as an Orthogonal Tool in Coiled Coil Assembly.
Biomacromolecules. 2023 Jul 10;24(7):3357-3369. doi: 10.1021/acs.biomac.3c00427. Epub 2023 Jun 28.
9
Desuccinylation-Triggered Peptide Self-Assembly: Live Cell Imaging of SIRT5 Activity and Mitochondrial Activity Modulation.
J Am Chem Soc. 2020 Oct 21;142(42):18150-18159. doi: 10.1021/jacs.0c08463. Epub 2020 Oct 11.
10
Membrane Association Allosterically Regulates Phospholipase A Enzymes and Their Specificity.
Acc Chem Res. 2022 Dec 6;55(23):3303-3311. doi: 10.1021/acs.accounts.2c00497. Epub 2022 Oct 31.
引用本文的文献
1
Tinker, Tailor, Soldier, Spy: The Diverse Roles That Fluorine Can Play within Amino Acid Side Chains.
Molecules. 2023 Aug 22;28(17):6192. doi: 10.3390/molecules28176192.
2
Synthesis, structural studies and biological properties of some phosphono-perfluorophenylalanine derivatives formed by SAr reactions.
RSC Adv. 2019 Aug 5;9(42):24117-24133. doi: 10.1039/c9ra03982a. eCollection 2019 Aug 2.
3
Systematic Evaluation of Fluorination as Modification for Peptide-Based Fusion Inhibitors against HIV-1 Infection.
Chembiochem. 2021 Dec 10;22(24):3443-3451. doi: 10.1002/cbic.202100417. Epub 2021 Oct 22.
4
Pd-Catalyzed Allylation of Imines to Access α-CF-Substituted α-Amino Acid Derivatives.
European J Org Chem. 2019 Nov 14;2019(42):7122-7127. doi: 10.1002/ejoc.201901272. Epub 2019 Oct 9.
5
Synthesis of α-CF-proline derivatives by means of a formal (3 + 2)-cyclisation between trifluoropyruvate imines and Michael acceptors.
Org Biomol Chem. 2019 Jun 12;17(23):5731-5735. doi: 10.1039/c9ob01134j.
6
Position-dependent impact of hexafluoroleucine and trifluoroisoleucine on protease digestion.
Beilstein J Org Chem. 2017 Dec 22;13:2869-2882. doi: 10.3762/bjoc.13.279. eCollection 2017.
7
Base-catalyzed diastereoselective trimerization of trifluoroacetone.
Org Biomol Chem. 2017 Jun 28;15(24):5131-5134. doi: 10.1039/c7ob01094j. Epub 2017 Jun 8.
8
Alpha-helical peptide assemblies giving new function to designed structures.
Prog Mol Biol Transl Sci. 2011;103:231-75. doi: 10.1016/B978-0-12-415906-8.00001-7.
9
Transferred NOESY NMR studies of biotin mimetic peptide (FSHPQNT) bound to streptavidin: a structural model for studies of peptide-protein interactions.
Chem Biol Drug Des. 2011 Jul;78(1):14-24. doi: 10.1111/j.1747-0285.2011.01096.x. Epub 2011 May 26.
10
Optimizing ¹⁹F NMR protein spectroscopy by fractional biosynthetic labeling.
J Biomol NMR. 2010 Oct;48(2):113-21. doi: 10.1007/s10858-010-9443-7. Epub 2010 Aug 24.
本文引用的文献
1
Fluorinated lipid constructs permit facile passage of molecular cargo into living cells.
J Am Chem Soc. 2009 Sep 2;131(34):12091-3. doi: 10.1021/ja902777d.
2
Properties and identification of human protein drug targets.
Bioinformatics. 2009 Feb 15;25(4):451-7. doi: 10.1093/bioinformatics/btp002. Epub 2009 Jan 21.
3
Biosynthesis and stability of coiled-coil peptides containing (2S,4R)-5,5,5-trifluoroleucine and (2S,4S)-5,5,5-trifluoroleucine.
Chembiochem. 2009 Jan 5;10(1):84-6. doi: 10.1002/cbic.200800164.
4
Expanding the fluorous arsenal: tetrafluorinated phenylalanines for protein design.
J Am Chem Soc. 2009 Jan 14;131(1):18-9. doi: 10.1021/ja8062309.
5
Influence of selective fluorination on the biological activity and proteolytic stability of glucagon-like peptide-1.
J Med Chem. 2008 Nov 27;51(22):7303-7. doi: 10.1021/jm8008579.
6
Fluorination of mammalian cell surfaces via the sialic acid biosynthetic pathway.
Bioorg Med Chem Lett. 2008 Nov 15;18(22):5945-7. doi: 10.1016/j.bmcl.2008.09.010. Epub 2008 Sep 6.
7
Structure and thermotropic phase behavior of fluorinated phospholipid bilayers: a combined attenuated total reflection FTIR spectroscopy and imaging ellipsometry study.
J Phys Chem B. 2008 Jul 17;112(28):8250-6. doi: 10.1021/jp800711j. Epub 2008 Jun 19.
8
Synthetic applications of fluorous solid-phase extraction (F-SPE).
Tetrahedron. 2006 Dec 18;62(51):11837-11865. doi: 10.1016/j.tet.2006.08.051.
9
Antimicrobial activity and protease stability of peptides containing fluorinated amino acids.
J Am Chem Soc. 2007 Dec 19;129(50):15615-22. doi: 10.1021/ja075373f. Epub 2007 Nov 28.
10
Amide bond formation with a new fluorous carbodiimide: separation by reverse fluorous solid-phase extraction.
Org Lett. 2007 Oct 11;9(21):4167-70. doi: 10.1021/ol701631m. Epub 2007 Sep 21.
Zotero 插件