Electrochemical synthesis of peptide aldehydes via C‒N bond cleavage of cyclic amines.

Aldehydes / chemistry Amines / chemistry Peptides / chemistry Electrochemical Techniques / methods Oxidation-Reduction Carbon / chemistry Peptides, Cyclic / chemistry Density Functional Theory

Journal

Nature communications
ISSN: 2041-1723
Titre abrégé: Nat Commun
Pays: England
ID NLM: 101528555

Informations de publication

Date de publication:
18 Jun 2024
Historique:
received: 28 12 2023
accepted: 29 05 2024
medline: 19 6 2024
pubmed: 19 6 2024
entrez: 18 6 2024
Statut: epublish

Résumé

Peptide aldehydes are crucial biomolecules essential to various biological systems, driving a continuous demand for efficient synthesis methods. Herein, we develop a metal-free, facile, and biocompatible strategy for direct electrochemical synthesis of unnatural peptide aldehydes. This electro-oxidative approach enabled a step- and atom-economical ring-opening via C‒N bond cleavage, allowing for homoproline-specific peptide diversification and expansion of substrate scope to include amides, esters, and cyclic amines of various sizes. The remarkable efficacy of the electro-synthetic protocol set the stage for the efficient modification and assembly of linear and macrocyclic peptides using a concise synthetic sequence with racemization-free conditions. Moreover, the combination of experiments and density functional theory (DFT) calculations indicates that different N-acyl groups play a decisive role in the reaction activity.

Identifiants

DOI: 10.1038/s41467-024-49223-y PMID: 38890290
pubmed: 38890290
doi: 10.1038/s41467-024-49223-y
pii: 10.1038/s41467-024-49223-y
doi:

Substances chimiques

Aldehydes 0
Amines 0
Peptides 0
Carbon 7440-44-0
Peptides, Cyclic 0

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

5181

Subventions

Organisme : National Natural Science Foundation of China (National Science Foundation of China)
ID : 22271067
Organisme : National Natural Science Foundation of China (National Science Foundation of China)
ID : 22201052

Informations de copyright

© 2024. The Author(s).

Références

Moulin, A., Martinez, J. & Fehrentz, J.-A. Synthesis of peptide aldehydes. J. Pept. Sci. 13, 1–15 (2007).
pubmed: 16998827 doi: 10.1002/psc.787
Dong, Y. et al. Closed-state inactivation and pore-blocker modulation mechanisms of human Ca(V)2.2. Cell Rep. 37, 109931–109942 (2021).
pubmed: 34731621 doi: 10.1016/j.celrep.2021.109931
Patel, K. D. et al. Novel cell-penetrating peptide conjugated proteasome inhibitors: anticancer and antifungal investigations. J. Med. Chem. 63, 334–348 (2020).
pubmed: 31801019 doi: 10.1021/acs.jmedchem.9b01694
Vidhya, R. & Anuradha, C. V. Anti-inflammatory effects of troxerutin are mediated through elastase inhibition. Immunopharmacol. Immunotoxicol. 42, 423–435 (2020).
pubmed: 32762381 doi: 10.1080/08923973.2020.1806870
Yan, R. et al. A structure of human Scap bound to Insig-2 suggests how their interaction is regulated by sterols. Science 371, eabb2224 (2021).
pubmed: 33446483 doi: 10.1126/science.abb2224
Andi, B. et al. Hepatitis C virus NS3/4A inhibitors and other drug-like compounds as covalent binders of SARS-CoV-2 main protease. Sci. Rep. 12, 12197–12208 (2022).
pubmed: 35842458 pmcid: 9287821 doi: 10.1038/s41598-022-15930-z
Fu, H., Park, J. & Pei, D. Peptidyl aldehydes as reversible covalent inhibitors of protein tyrosine phosphatases. Biochemistry 41, 10700–10709 (2002).
pubmed: 12186556 doi: 10.1021/bi0258748
Murar, C. E., Thuaud, F. & Bode, J. W. KAHA ligations that form aspartyl aldehyde residues as synthetic handles for protein modification and purification. J. Am. Chem. Soc. 136, 18140–18148 (2014).
pubmed: 25474323 doi: 10.1021/ja511231f
Rabuka, D., Rush, J. S., deHart, G. W., Wu, P. & Bertozzi, C. R. Site-specific chemical protein conjugation using genetically encoded aldehyde tags. Nat. Protoc. 7, 1052–1067 (2012).
pubmed: 22576105 pmcid: 3498491 doi: 10.1038/nprot.2012.045
Malins, L. R. et al. Peptide macrocyclization inspired by non-ribosomal imine natural products. J. Am. Chem. Soc. 139, 5233–5241 (2017).
pubmed: 28326777 pmcid: 5391502 doi: 10.1021/jacs.7b01624
Hayashi, Y., Hirose, T., Iwatsuki, M., O̅mura, S. & Sunazuka, T. Synthesis of the antimalarial peptide aldehyde, a precursor of Kozupeptin A, utilizing a designed hydrophobic anchor molecule. Org. Lett. 21, 8229–8233 (2019).
pubmed: 31524407 doi: 10.1021/acs.orglett.9b02966
Al-Gharabli, S. I. et al. An efficient method for the synthesis of peptide aldehyde libraries employed in the discovery of reversible SARS coronavirus main protease (SARS-CoV Mpro) inhibitors. ChemBioChem 7, 1048–1055 (2006).
pubmed: 16688706 pmcid: 7417790 doi: 10.1002/cbic.200500533
Aho, A., Sulkanen, M., Korhonen, H. & Virta, P. Conjugation of oligonucleotides to peptide aldehydes via a Ph-responsive N-methoxyoxazolidine linker. Org. Lett. 22, 6714–6718 (2020).
pubmed: 32804515 doi: 10.1021/acs.orglett.0c01815
Konno, H., Sema, Y. & Tokairin, Y. Synthetic study of peptide aldehyde via acetal/thioacetal transformation: application for Lys/Ser-containing peptides. Tetrahedron 71, 3433–3438 (2015).
doi: 10.1016/j.tet.2015.03.080
Kang, W. et al. A simple oxazolidine linker for solid-phase synthesis of peptide aldehydes. Bioorg. Med. Chem. Lett. 22, 1187–1188 (2012).
pubmed: 22196121 doi: 10.1016/j.bmcl.2011.11.081
Ede, N. J., Hill, J., Joy, J. K., Ede, A.-M. & Koppens, M. L. Solid-phase synthesis and screening of a library of C-terminal arginine peptide aldehydes against Murray Valley encephalitis virus protease. J. Pept. Sci. 18, 661–668 (2012).
pubmed: 22991186 pmcid: 7167811 doi: 10.1002/psc.2450
Yan, M., Kawamata, Y. & Baran, P. S. Synthetic organic electrochemical methods since 2000: on the verge of a renaissance. Chem. Rev. 117, 13230–13319 (2017).
pubmed: 28991454 pmcid: 5786875 doi: 10.1021/acs.chemrev.7b00397
Meyer, T. H., Choi, I., Tian, C. & Ackermann, L. Powering the future: how can electrochemistry make a difference in organic synthesis? Chem 6, 2484–2496 (2020).
doi: 10.1016/j.chempr.2020.08.025
Tay, N. E. S., Lehnherr, D. & Rovis, T. Photons or electrons? A critical comparison of electrochemistry and photoredox catalysis for organic synthesis. Chem. Rev. 122, 2487–2649 (2021).
pubmed: 34751568 pmcid: 10021920 doi: 10.1021/acs.chemrev.1c00384
Zhu, C., Ang, N. W. J., Meyer, T. H., Qiu, Y. & Ackermann, L. Organic electrochemistry: molecular syntheses with potential. ACS Cent. Sci. 7, 415–431 (2021).
pubmed: 33791425 pmcid: 8006177 doi: 10.1021/acscentsci.0c01532
Cheng, X. et al. Recent applications of homogeneous catalysis in electrochemical organic synthesis. CCS Chem. 4, 1120–1152 (2022).
doi: 10.31635/ccschem.021.202101451
Wang, H., Gao, X., Lv, Z., Abdelilah, T. & Lei, A. Recent advances in oxidative R1-H/R2-H cross-coupling with hydrogen evolution via photo-/electrochemistry. Chem. Rev. 119, 6769–6787 (2019).
pubmed: 31074264 doi: 10.1021/acs.chemrev.9b00045
Xiong, P. & Xu, H.-C. Chemistry with electrochemically generated N-centered radicals. Acc. Chem. Res. 52, 3339–3350 (2019).
pubmed: 31774646 doi: 10.1021/acs.accounts.9b00472
Yuan, Y. & Lei, A. Electrochemical oxidative cross-coupling with hydrogen evolution reactions. Acc. Chem. Res. 52, 3309–3324 (2019).
pubmed: 31774271 doi: 10.1021/acs.accounts.9b00512
Ackermann, L. Metalla-electrocatalyzed C–H activation by Earth-abundant 3d metals and beyond. Acc. Chem. Res. 53, 84–104 (2020).
pubmed: 31854967 doi: 10.1021/acs.accounts.9b00510
Jiao, K.-J., Xing, Y.-K., Yang, Q.-L., Qiu, H. & Mei, T.-S. Site-selective C–H functionalization via synergistic use of electrochemistry and transition metal catalysis. Acc. Chem. Res. 53, 300–310 (2020).
pubmed: 31939278 doi: 10.1021/acs.accounts.9b00603
Leech, M. C. & Lam, K. Electrosynthesis using carboxylic acid derivatives: new tricks for old reactions. Acc. Chem. Res. 53, 121–134 (2020).
pubmed: 31895535 doi: 10.1021/acs.accounts.9b00586
Minteer, S. D. & Baran, P. Electrifying synthesis: recent advances in the methods, materials, and techniques for organic electrosynthesis. Acc. Chem. Res. 53, 545–546 (2020).
pubmed: 32178522 doi: 10.1021/acs.accounts.0c00049
Röckl, J. L., Pollok, D., Franke, R. & Waldvogel, S. R. A decade of electrochemical dehydrogenative C,C-coupling of aryls. Acc. Chem. Res. 53, 45–61 (2020).
pubmed: 31850730 doi: 10.1021/acs.accounts.9b00511
Siu, J. C., Fu, N. & Lin, S. Catalyzing electrosynthesis: a homogeneous electrocatalytic approach to reaction discovery. Acc. Chem. Res. 53, 547–560 (2020).
pubmed: 32077681 pmcid: 7245362 doi: 10.1021/acs.accounts.9b00529
Brabec, V. & Mornstein, V. Electrochemical behaviour of proteins at graphite electrodes: II. Electrooxidation of amino acids. Biophys. Chem. 12, 159–165 (1980).
pubmed: 17000148 doi: 10.1016/0301-4622(80)80048-2
Sęk, S., Vacek, J. & Dorčák, V. Electrochemistry of peptides. Curr. Opin. Electrochem. 14, 166–172 (2019).
doi: 10.1016/j.coelec.2019.03.002
Mackay, A. S., Payne, R. J. & Malins, L. R. Electrochemistry for the chemoselective modification of peptides and proteins. J. Am. Chem. Soc. 144, 23–41 (2022).
pubmed: 34968405 doi: 10.1021/jacs.1c11185
Liang, Y. et al. Electrochemically induced nickel catalysis for oxygenation reactions with water. Nat. Catal. 4, 116–123 (2021).
doi: 10.1038/s41929-020-00559-w
Cai, C.-Y. et al. Photoelectrochemical asymmetric catalysis enables site- and enantioselective cyanation of benzylic C–H bonds. Nat. Catal. 5, 943–951 (2022).
doi: 10.1038/s41929-022-00855-7
Lai, X.-L., Chen, M., Wang, Y., Song, J. & Xu, H.-C. Photoelectrochemical asymmetric catalysis enables direct and enantioselective decarboxylative cyanation. J. Am. Chem. Soc. 144, 20201–20206 (2022).
pubmed: 36315651 doi: 10.1021/jacs.2c09050
Long, H. et al. Electrochemical C–H phosphorylation of arenes in continuous flow suitable for late-stage functionalization. Nat. Commun. 12, 6629–6635 (2021).
pubmed: 34785664 pmcid: 8616953 doi: 10.1038/s41467-021-26960-y
Xiong, P. et al. Site-selective electrooxidation of methylarenes to aromatic acetals. Nat. Commun. 11, 2706–2713 (2020).
pubmed: 32483217 pmcid: 7264330 doi: 10.1038/s41467-020-16519-8
Ruan, Z. et al. Late-stage azolation of benzylic C‒H bonds enabled by electrooxidation. Sci. China Chem. 64, 800–807 (2021).
doi: 10.1007/s11426-020-9938-9
Hou, X. et al. Ruthenaelectro-catalyzed C–H acyloxylation for late-stage tyrosine and oligopeptide diversification. Chem. Sci. 13, 3461–3467 (2022).
pubmed: 35432858 pmcid: 8943857 doi: 10.1039/D1SC07267F
Sato, S. et al. Site-selective protein chemical modification of exposed tyrosine residues using tyrosine click reaction. Bioconjugate Chem. 31, 1417–1424 (2020).
doi: 10.1021/acs.bioconjchem.0c00120
Song, C. et al. Electrochemical oxidation induced selective tyrosine bioconjugation for the modification of biomolecules. Chem. Sci. 10, 7982–7987 (2019).
pubmed: 31673320 pmcid: 6788519 doi: 10.1039/C9SC02218J
Alvarez-Dorta, D. et al. Electrochemically promoted tyrosine-click-chemistry for protein labeling. J. Am. Chem. Soc. 140, 17120–17126 (2018).
pubmed: 30422648 doi: 10.1021/jacs.8b09372
Depienne, S. et al. Luminol anchors improve the electrochemical-tyrosine-click labelling of proteins. Chem. Sci. 12, 15374–15381 (2021).
pubmed: 34976358 pmcid: 8635215 doi: 10.1039/D1SC04809K
You, S. et al. Electrochemical chemoselective hydroxyl group transformation: anthranilic acyl modification of tyrosine bioconjugations. Org. Chem. Front. 10, 4606–4615 (2023).
doi: 10.1039/D3QO00983A
Toyama, E. et al. Electrochemical tryptophan-selective bioconjugation. ChemRxiv. https://doi.org/10.26434/chemrxiv.7795484.v1 (2019).
Weng, Y., Xu, X., Chen, H., Zhang, Y. & Zhuo, X. Tandem electrochemical oxidative azidation/heterocyclization of tryptophan-containing peptides under buffer conditions. Angew. Chem. Int. Ed. 61, e202206308 (2022).
doi: 10.1002/anie.202206308
Dutta, S., Li, B., Rickertsen, D. R. L., Valles, D. A. & Seidel, D. C–H bond functionalization of amines: a graphical overview of diverse methods. SynOpen 5, 173–228 (2021).
pubmed: 34825124 pmcid: 8612105 doi: 10.1055/s-0040-1706051
Osberger, T. J., Rogness, D. C., Kohrt, J. T., Stepan, A. F. & White, M. C. Oxidative diversification of amino acids and peptides by small-molecule iron catalysis. Nature 537, 214–219 (2016).
pubmed: 27479323 pmcid: 5161617 doi: 10.1038/nature18941
Roque, J. B., Kuroda, Y., Göttemann, L. T. & Sarpong, R. Deconstructive fluorination of cyclic amines by carbon-carbon cleavage. Science 361, 171–174 (2018).
pubmed: 30002251 pmcid: 6287955 doi: 10.1126/science.aat6365
Kim, Y., Heo, J., Kim, D., Chang, S. & Seo, S. Ring-opening functionalizations of unstrained cyclic amines enabled by difluorocarbene transfer. Nat. Commun. 11, 4761–4771 (2020).
pubmed: 32958762 pmcid: 7506026 doi: 10.1038/s41467-020-18557-8
Ham, J. S. et al. C–H/C–C functionalization approach to N-fused heterocycles from saturated azacycles. J. Am. Chem. Soc. 142, 13041–13050 (2020).
pubmed: 32627545 pmcid: 7773224 doi: 10.1021/jacs.0c04278
Roque, J. B., Kuroda, Y., Göttemann, L. T. & Sarpong, R. Deconstructive diversification of cyclic amines. Nature 564, 244–248 (2018).
pubmed: 30382193 pmcid: 6317721 doi: 10.1038/s41586-018-0700-3
Jurczyk, J. et al. Photomediated ring contraction of saturated heterocycles. Science 373, 1004–1012 (2021).
pubmed: 34385352 pmcid: 8627180 doi: 10.1126/science.abi7183
Chen, W., Ma, L., Paul, A. & Seidel, D. Direct α-C–H bond functionalization of unprotected cyclic amines. Nat. Chem. 10, 165–169 (2018).
pubmed: 29359746 doi: 10.1038/nchem.2871
Lennox, A. J. J. et al. Electrochemical aminoxyl-mediated α-cyanation of secondary piperidines for pharmaceutical building block diversification. J. Am. Chem. Soc. 140, 11227–11231 (2018).
pubmed: 30141925 pmcid: 6178801 doi: 10.1021/jacs.8b08145
Taylor, R. D., MacCoss, M. & Lawson, A. D. G. Rings in drugs. J. Med. Chem. 57, 5845–5859 (2014).
pubmed: 24471928 doi: 10.1021/jm4017625
Shearer, J., Castro, J. L., Lawson, A. D. G., MacCoss, M. & Taylor, R. D. Rings in clinical trials and drugs: present and future. J. Med. Chem. 65, 8699–8712 (2022).
pubmed: 35730680 pmcid: 9289879 doi: 10.1021/acs.jmedchem.2c00473
Shono, T., Hamaguchi, H. & Matsumura, Y. Electroorganic chemistry. XX. Anodic oxidation of carbamates. J. Am. Chem. Soc. 97, 4264–4268 (1975).
doi: 10.1021/ja00848a020
Shono, T., Matsumura, Y. & Tsubata, K. Electroorganic chemistry. 46. A new carbon-carbon bond forming reaction at the.alpha.-position of amines utilizing anodic oxidation as a key step. J. Am. Chem. Soc. 103, 1172–1176 (1981).
doi: 10.1021/ja00395a029
Wang, F., Rafiee, M. & Stahl, S. S. Electrochemical functional-group-tolerant shono-type oxidation of cyclic carbamates enabled by aminoxyl mediators. Angew. Chem. Int. Ed. 57, 6686–6690 (2018).
doi: 10.1002/anie.201803539
Zeng, S. et al. Selenium-electrocatalytic cyclization of 2-vinylanilides towards indoles of peptide labeling. Chem. Asian J. 17, e202200762 (2022).
pubmed: 35986904 doi: 10.1002/asia.202200762
Fang, X., Huang, Y., Hu, X. & Ruan, Z. Recent progress in electrochemical modification of amino acids and peptides. Chin. J. Org. Chem. 44, 903–926 (2024).
doi: 10.6023/cjoc202310024
Feng, T. et al. Electrochemical dual α,β-C(sp3)–H functionalization of cyclic N-aryl amines. Green. Chem. 25, 2681–2689 (2023).
doi: 10.1039/D3GC00344B
Feng, T., Wang, S., Liu, Y., Liu, S. & Qiu, Y. Electrochemical desaturative β-acylation of cyclic N-aryl amines. Angew. Chem. Int. Ed. 61, e202115178 (2022).
doi: 10.1002/anie.202115178
Peacock, H. & Suga, H. Discovery of De Novo macrocyclic peptides by messenger RNA display. Trends Pharmacol. Sci. 42, 385–397 (2021).
pubmed: 33771353 doi: 10.1016/j.tips.2021.02.004
Vinogradov, A. A., Yin, Y. & Suga, H. Macrocyclic peptides as drug candidates: recent progress and remaining challenges. J. Am. Chem. Soc. 141, 4167–4181 (2019).
pubmed: 30768253 doi: 10.1021/jacs.8b13178
Passioura, T., Katoh, T., Goto, Y. & Suga, H. Selection-based discovery of druglike macrocyclic peptides. Annu. Rev. Biochem. 83, 727–752 (2014).
pubmed: 24580641 doi: 10.1146/annurev-biochem-060713-035456
Driggers, E. M., Hale, S. P., Lee, J. & Terrett, N. K. The exploration of macrocycles for drug discovery—an underexploited structural class. Nat. Rev. Drug Discov. 7, 608–624 (2008).
pubmed: 18591981 doi: 10.1038/nrd2590
Ruan, Z., Sauermann, N., Manoni, E. & Ackermann, L. Manganese-catalyzed C-H alkynylation: expedient peptide synthesis and modification. Angew. Chem. Int. Ed. 56, 3172–3176 (2017).
doi: 10.1002/anie.201611118
Dong, J. J., Harvey, E. C., Fañanás-Mastral, M., Browne, W. R. & Feringa, B. L. Palladium-catalyzed anti-markovnikov oxidation of allylic amides to protected β-amino aldehydes. J. Am. Chem. Soc. 136, 17302–17307 (2014).
pubmed: 25384246 doi: 10.1021/ja510163w
Shpak-Kraievskyi, P. et al. Access to C-protected β-amino-aldehydes via transacetalization of 6-alcoxy tetrahydrooxazinones and use for pseudo-peptide synthesis. Tetrahedron 68, 2179–2188 (2012).
doi: 10.1016/j.tet.2012.01.002
Soro, D. M. et al. Photo- and metal-mediated deconstructive approaches to cyclic aliphatic amine diversification. J. Am. Chem. Soc. 145, 11245–11257 (2023).
pubmed: 37171220 pmcid: 10214453 doi: 10.1021/jacs.3c01318
Wang, F. & Frankowski, K. J. Divergent electrochemical carboamidation of cyclic amines. J. Org. Chem. 87, 1173–1193 (2022).
pubmed: 34985905 doi: 10.1021/acs.joc.1c02534
Gao, P.-S. et al. CuII/TEMPO-catalyzed enantioselective C(sp3)–H alkynylation of tertiary cyclic amines through shono-type oxidation. Angew. Chem. Int. Ed. 59, 15254–15259 (2020).
doi: 10.1002/anie.202005099

Auteurs

Xinyue Fang (X)

Guangzhou Municipal and Guangdong Provincial Key Laboratory of Molecular Target & Clinical Pharmacology and the State Key Laboratory of Respiratory Disease, School of Pharmaceutical Sciences & the Fifth Affiliated Hospital, Guangzhou Medical University, Guangzhou, 511436, PR China.

Yong Zeng (Y)

Guangzhou Municipal and Guangdong Provincial Key Laboratory of Molecular Target & Clinical Pharmacology and the State Key Laboratory of Respiratory Disease, School of Pharmaceutical Sciences & the Fifth Affiliated Hospital, Guangzhou Medical University, Guangzhou, 511436, PR China.

Yawen Huang (Y)

Guangzhou Municipal and Guangdong Provincial Key Laboratory of Molecular Target & Clinical Pharmacology and the State Key Laboratory of Respiratory Disease, School of Pharmaceutical Sciences & the Fifth Affiliated Hospital, Guangzhou Medical University, Guangzhou, 511436, PR China.

Zile Zhu (Z)

State Key Laboratory and Institute of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, 94 Weijin Road, Tianjin, 300071, PR China.

Shengsheng Lin (S)

Guangzhou Municipal and Guangdong Provincial Key Laboratory of Molecular Target & Clinical Pharmacology and the State Key Laboratory of Respiratory Disease, School of Pharmaceutical Sciences & the Fifth Affiliated Hospital, Guangzhou Medical University, Guangzhou, 511436, PR China.

Wenyan Xu (W)

Guangzhou Municipal and Guangdong Provincial Key Laboratory of Molecular Target & Clinical Pharmacology and the State Key Laboratory of Respiratory Disease, School of Pharmaceutical Sciences & the Fifth Affiliated Hospital, Guangzhou Medical University, Guangzhou, 511436, PR China.

Chengwei Zheng (C)

Guangzhou Municipal and Guangdong Provincial Key Laboratory of Molecular Target & Clinical Pharmacology and the State Key Laboratory of Respiratory Disease, School of Pharmaceutical Sciences & the Fifth Affiliated Hospital, Guangzhou Medical University, Guangzhou, 511436, PR China.

Xinwei Hu (X)

Guangzhou Municipal and Guangdong Provincial Key Laboratory of Molecular Target & Clinical Pharmacology and the State Key Laboratory of Respiratory Disease, School of Pharmaceutical Sciences & the Fifth Affiliated Hospital, Guangzhou Medical University, Guangzhou, 511436, PR China. xinweihu@gzhmu.edu.cn.

Youai Qiu (Y)

State Key Laboratory and Institute of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, 94 Weijin Road, Tianjin, 300071, PR China. qiuyouai@nankai.edu.cn.
ORCID: 0000-0002-5859-6754

Zhixiong Ruan (Z)

Guangzhou Municipal and Guangdong Provincial Key Laboratory of Molecular Target & Clinical Pharmacology and the State Key Laboratory of Respiratory Disease, School of Pharmaceutical Sciences & the Fifth Affiliated Hospital, Guangzhou Medical University, Guangzhou, 511436, PR China. zruan@gzhmu.edu.cn.
ORCID: 0000-0002-5433-2460

Articles similaires

Environmental impact assessment of Flora and its role in offsetting carbon along National Highway-16, India.

H Ramamohan, S Raminaidu, I Sudhakara Rao et al.
1.00
India Carbon Sequestration Environmental Monitoring Carbon Biomass

A molecular mechanism for bright color variation in parrots.

Roberto Arbore, Soraia Barbosa, Jindich Brejcha et al.
1.00
Animals Feathers Pigmentation Parrots Aldehyde Dehydrogenase

Proteomimetic polymer blocks mitochondrial damage, rescues Huntington's neurons, and slows onset of neuropathology in vivo.

Wonmin Choi, Mara Fattah, Yutong Shang et al.
1.00
Animals Huntington Disease Mitochondria Neurons Mice

Saccharomyces cerevisiae whole cell biotransformation for the production of aldehyde flavors and fragrances.

Nazreen V M Abdul Muthaliff, Yao Zong Ng, Wei Mei Guo et al.
1.00
Saccharomyces cerevisiae Aldehydes Biotransformation Flavoring Agents Lipoxygenase

Classifications MeSH

questionsmedicales.fr › Composés chimiques organiques › Aldéhydes › Electrochemical synthesis of peptide aldehydes...
questionsmedicales.fr › Composés chimiques organiques › Amines › Electrochemical synthesis of peptide aldehydes...
questionsmedicales.fr › Acides aminés, peptides et protéines › Peptides › Electrochemical synthesis of peptide aldehydes...
questionsmedicales.fr › Techniques d'investigation › Techniques électrochimiques › Electrochemical synthesis of peptide aldehydes...
questionsmedicales.fr › Métabolisme › Métabolisme énergétique › Oxydoréduction › Electrochemical synthesis of peptide aldehydes...
questionsmedicales.fr › Produits chimiques inorganiques › Éléments › Carbone › Electrochemical synthesis of peptide aldehydes...
questionsmedicales.fr › Acides aminés, peptides et protéines › Peptides › Peptides cycliques › Electrochemical synthesis of peptide aldehydes...
questionsmedicales.fr › Disciplines des sciences naturelles › Physique › Physique nucléaire › Théorie quantique › Théorie de la fonctionnelle de la densité › Electrochemical synthesis of peptide aldehydes...