具有ω-生物正交叠氮化物和炔烃官能团的法尼基二磷酸类似物用于蛋白质法尼基转移酶催化的连接反应。
Farnesyl diphosphate analogues with omega-bioorthogonal azide and alkyne functional groups for protein farnesyl transferase-catalyzed ligation reactions.
作者信息
Labadie Guillermo R, Viswanathan Rajesh, Poulter C Dale
机构信息
Department of Chemistry, University of Utah, Salt Lake City, UT 84112, USA.
出版信息
J Org Chem. 2007 Nov 23;72(24):9291-7. doi: 10.1021/jo7017747. Epub 2007 Nov 3.
Abstract
Eleven farnesyl diphosphate analogues, which contained omega-azide or alkyne substituents suitable for bioorthogonal Staudinger and Huisgen [3 + 2] cycloaddition coupling reactions, were synthesized. The analogues were evaluated as substrates for the alkylation of peptide cosubstrates by yeast protein farnesyl transferase. Five of the diphosphates were good alternative substrates for farnesyl diphosphate (FPP). Steady-state kinetic constants were measured for the active compounds, and the products were characterized by HPLC and LC-MS. Two of the analogues gave steady-state kinetic parameters (kcat and Km) very similar to those of the natural substrate.
摘要
合成了11种法尼基二磷酸类似物，这些类似物含有适用于生物正交施陶丁格反应和惠斯根[3 + 2]环加成偶联反应的ω-叠氮基或炔基取代基。这些类似物被评估为酵母蛋白法尼基转移酶对肽共底物进行烷基化反应的底物。其中五种二磷酸是法尼基二磷酸（FPP）的良好替代底物。测定了活性化合物的稳态动力学常数，并通过高效液相色谱（HPLC）和液相色谱-质谱联用（LC-MS）对产物进行了表征。其中两种类似物给出的稳态动力学参数（kcat和Km）与天然底物的非常相似。
相似文献
1
Farnesyl diphosphate analogues with omega-bioorthogonal azide and alkyne functional groups for protein farnesyl transferase-catalyzed ligation reactions.
J Org Chem. 2007 Nov 23;72(24):9291-7. doi: 10.1021/jo7017747. Epub 2007 Nov 3.
2
Photoaffinity analogues of farnesyl pyrophosphate transferable by protein farnesyl transferase.
J Am Chem Soc. 2002 Jul 17;124(28):8206-19. doi: 10.1021/ja0124717.
3
Selective modification of CaaX peptides with ortho-substituted anilinogeranyl lipids by protein farnesyl transferase: competitive substrates and potent inhibitors from a library of farnesyl diphosphate analogues.
Biochemistry. 2007 Oct 9;46(40):11310-21. doi: 10.1021/bi700516m. Epub 2007 Sep 14.
4
Farnesyl diphosphate analogues with aryl moieties are efficient alternate substrates for protein farnesyltransferase.
Biochemistry. 2012 Oct 16;51(41):8307-19. doi: 10.1021/bi3011362. Epub 2012 Oct 2.
5
From mechanism to mouse: a tale of two bioorthogonal reactions.
Acc Chem Res. 2011 Sep 20;44(9):666-76. doi: 10.1021/ar200148z. Epub 2011 Aug 15.
6
Analogs of farnesyl diphosphate alter CaaX substrate specificity and reactions rates of protein farnesyltransferase.
Bioorg Med Chem Lett. 2016 Feb 15;26(4):1333-6. doi: 10.1016/j.bmcl.2015.12.079. Epub 2015 Dec 22.
7
Synthesis of acyloxymethyl ester prodrugs of the transferable protein farnesyl transferase substrate farnesyl methylenediphosphonate.
Bioorg Med Chem Lett. 2004 Oct 4;14(19):4979-82. doi: 10.1016/j.bmcl.2004.07.017.
8
Yeast protein farnesyltransferase. Binding of S-alkyl peptides and related analogues.
Org Lett. 1999 Sep 9;1(5):815-7. doi: 10.1021/ol990814o.
9
Synthesis of frame-shifted farnesyl diphosphate analogs.
Org Lett. 2012 Aug 17;14(16):4038-41. doi: 10.1021/ol300683r. Epub 2012 Aug 2.
10
Hydrophilic anilinogeranyl diphosphate prenyl analogues are Ras function inhibitors.
Biochemistry. 2006 Dec 26;45(51):15862-72. doi: 10.1021/bi061704+. Epub 2006 Dec 6.
引用本文的文献
1
Structure-Activity Relationship Study of Cannabidiol-Based Analogs as Negative Allosteric Modulators of the μ-Opioid Receptor.
J Med Chem. 2023 Jul 27;66(14):9466-9494. doi: 10.1021/acs.jmedchem.3c00061. Epub 2023 Jul 12.
2
Promiscuous Enzymes for Residue-Specific Peptide and Protein Late-Stage Functionalization.
Chembiochem. 2023 Sep 1;24(17):e202300372. doi: 10.1002/cbic.202300372. Epub 2023 Jul 19.
3
Chemoenzymatic Preparation of a Lipid-Linked Heptasaccharide on an Azide-Linked Polyisoprenoid.
ACS Omega. 2023 Apr 22;8(17):15790-15798. doi: 10.1021/acsomega.3c01657. eCollection 2023 May 2.
4
A Not-So-Ancient Grease History: Click Chemistry and Protein Lipid Modifications.
Chem Rev. 2021 Jun 23;121(12):7178-7248. doi: 10.1021/acs.chemrev.0c01108. Epub 2021 Apr 6.
5
GLOBAL AND TARGETED PROFILING OF GTP-BINDING PROTEINS IN BIOLOGICAL SAMPLES BY MASS SPECTROMETRY.
Mass Spectrom Rev. 2021 May;40(3):215-235. doi: 10.1002/mas.21637. Epub 2020 Jun 10.
6
Repositioning Salirasib as a new antimalarial agent.
Medchemcomm. 2019 Jun 21;10(9):1599-1605. doi: 10.1039/c9md00298g. eCollection 2019 Sep 1.
7
Recent progress in enzymatic protein labelling techniques and their applications.
Chem Soc Rev. 2018 Dec 21;47(24):9106-9136. doi: 10.1039/c8cs00537k. Epub 2018 Sep 27.
8
Antitrypanosomal and antileishmanial activity of prenyl-1,2,3-triazoles.
Medchemcomm. 2017 May 1;8(5):1015-1021. doi: 10.1039/C7MD00008A. Epub 2017 Mar 10.
9
Site-Specific and Stoichiometric Stealth Polymer Conjugates of Therapeutic Peptides and Proteins.
Bioconjug Chem. 2017 Mar 15;28(3):713-723. doi: 10.1021/acs.bioconjchem.6b00652. Epub 2017 Jan 6.
10
Exploration of GGTase-I substrate requirements. Part 2: Synthesis and biochemical analysis of novel saturated geranylgeranyl diphosphate analogs.
Bioorg Med Chem Lett. 2016 Aug 1;26(15):3503-7. doi: 10.1016/j.bmcl.2016.06.035. Epub 2016 Jun 15.
本文引用的文献
1
Chemo-Enzymatic Synthesis of Fluorescent Rab 7 Proteins: Tools to Study Vesicular Trafficking in Cells.
Angew Chem Int Ed Engl. 1999 Feb 15;38(4):509-512. doi: 10.1002/(SICI)1521-3773(19990215)38:4<509::AID-ANIE509>3.0.CO;2-3.
2
A photoactive isoprenoid diphosphate analogue containing a stable phosphonate linkage: synthesis and biochemical studies with prenyltransferases.
J Org Chem. 2007 Jun 22;72(13):4587-95. doi: 10.1021/jo0623033. Epub 2007 May 4.
3
Exploiting the substrate tolerance of farnesyltransferase for site-selective protein derivatization.
Chembiochem. 2007 Mar 5;8(4):408-23. doi: 10.1002/cbic.200600440.
4
Selective labeling of proteins by using protein farnesyltransferase.
Chembiochem. 2007 Jan 2;8(1):98-105. doi: 10.1002/cbic.200600340.
5
Prelamin A farnesylation and progeroid syndromes.
J Biol Chem. 2006 Dec 29;281(52):39741-5. doi: 10.1074/jbc.R600033200. Epub 2006 Nov 7.
6
Structurally simple, potent, Plasmodium selective farnesyltransferase inhibitors that arrest the growth of malaria parasites.
J Med Chem. 2006 Sep 21;49(19):5710-27. doi: 10.1021/jm060081v.
7
Protein farnesyltransferase inhibitors and progeria.
Trends Mol Med. 2006 Oct;12(10):480-7. doi: 10.1016/j.molmed.2006.08.006. Epub 2006 Aug 30.
8
Regio- and chemoselective covalent immobilization of proteins through unnatural amino acids.
J Am Chem Soc. 2006 Jul 26;128(29):9274-5. doi: 10.1021/ja061131o.
9
Site-specific, covalent attachment of proteins to a solid surface.
Bioconjug Chem. 2006 Jul-Aug;17(4):967-74. doi: 10.1021/bc060125e.
10
Chemistry in living systems.
Nat Chem Biol. 2005 Jun;1(1):13-21. doi: 10.1038/nchembio0605-13.
Zotero 插件