Recent progress of on-resin cyclization for the synthesis of clycopeptidomimetics
- Corresponding author: Wu Zhi-Meng, zwu@jiangnan.edu.cn
Citation:
Wu Zhi-Meng, Liu Shao-Zhong, Cheng Xiao-Zhong, Ding Wen-Zhang, Zhu Tao, Chen Bing. Recent progress of on-resin cyclization for the synthesis of clycopeptidomimetics[J]. Chinese Chemical Letters,
;2016, 27(12): 1731-1739.
doi:
10.1016/j.cclet.2016.04.024
(a) E. Marsault, M.L. Peterson, Macrocycles are great cycles:applications, opportunities, and challenges of synthetic macrocycles in drug discovery, J. Med. Chem. 54(2011) 1961-2004;(b) E.M. Driggers, S.P. Hale, J. Lee, N.K. Terrett, The exploration of macrocycles for drug discovery-an underexploited structural class, Nat. Rev. Drug Discov. 7(2008) 608-624;(c) L.A. Wessjohann, E. Ruijter, D. Garcia-Rivera, W. Brandt, What can a chemist learn from nature's macrocycles?-a brief, conceptual view, Mol. Divers. 9(2005) 171-186;(d) V. Marti-Centelles, M.D. Pandey, M.I. Burguete, S.V. Luis, Macrocyclization reactions:the importance of conformational, configurational, and template-induced preorganization, Chem. Rev. 115(2015) 8736-8834;(e) A.K. Yudin, Macrocycles:lessons from the distant past, recent developments, and future directions, Chem. Sci. 6(2015) 30-49.
(a) L. Gentilucci, R. De Marco, L. Cerisoli, Chemical modifications designed to improve peptide stability:incorporation of non-natural amino acids, pseudopeptide bonds, and cyclization, Curr. Pharm. Des. 16(2010) 3185-3203;(b) C. Adessi, C. Soto, Converting a peptide into a drug:strategies to improve stability and bioavailability, Curr. Med. Chem. 9(2002) 963-978;(c) G.M. Pauletti, S. Gangwar, T.J. Siahaan, J. Aube, R.T. Borchardt, Improvement of oral peptide bioavailability:peptidomimetics and prodrug strategies, Adv. Drug Deliv. Rev. 27(1997) 235-256;(d) P.S. Burton, R.A. Conradi, N.F.H. Ho, A.R. Hilgers, R.T. Borchardt, How structural features influence the biomembrane permeability of peptides, J. Pharm. Sci. 85(1996) 1336-1340.
(a) J. Mallinson, I. Collins, Macrocycles in new drug discovery, Future Med. Chem. 4(2012) 1409-1438;(b) S. Jiang, Z. Li, K. Ding, P.P. Roller, Recent progress of synthetic studies to peptide and peptidomimetic cyclization, Curr. Org. Chem. 12(2008) 1502-1542;(c) P. Bulet, R. Stocklin, L. Menin, Anti-microbial peptides:from invertebrates to vertebrates, Immunol. Rev. 198(2004) 169-184.
C.J White, A.K Yudin. Contemporary strategies for peptide macrocyclization[J]. Nat. Chem, 2011,3:509-524. doi: 10.1038/nchem.1062
J.C Collins, K James. Emac-a comparative index for the assessment of macrocyclization efficiency[J]. Med. Chem. Comm, 2012,3:1489-1495.
(a) M. Malesevic, U. Strijowski, D. Bachle, N. Sewald, An improved method for the solution cyclization of peptides under pseudo-high dilution conditions, J. Biotechnol. 112(2004) 73-77;(b) T.S. Lawrence, R. Julius, O. Leonid, L.S. Charles, Organic chemistry on the solid phase. Site-site interactions on functionalized polystyrene, J. Am. Chem. Soc. 99(1977) 626-627;(c) Z. Liu, G.J. Tian, D.X. Wang, An efficient synthesis of cyclopeptides bridged with aliphatic-aryl ether bond, Chin. Chem. Lett. 16(2005) 759-762.
(a) V. Castro, H. Rodriguez, F. Albericio, CuAAC:an efficient click chemistry reaction on solid phase, ACS Comb. Sci. 18(2016) 1-14;(b) M. Meldal, C.W. Tornoe, Cu-catalyzed azide-alkyne cycloaddition, Chem. Rev. 108(2008) 2952-3015;(c) J.E. Moses, A.D. Moorhouse, The growing applications of click chemistry, Chem. Soc. Rev. 36(2007) 1249-1262;(d) H.C. Kolb, M.G. Finn, K.B. Sharpless, Click chemistry:diverse chemical function from a few good reactions, Angew. Chem. Int. Ed. 40(2001) 2004-2021.
(a) I.E. Valverde, A. Bauman, C.A. Kluba, et al., 2,3-triazoles as amide bond mimics:triazole scan yields protease-resistant peptidomimetics for tumor targeting, Angew. Chem. Int. Ed. 52(2013) 8957-8960;(b) G.C. Tron, T. Pirali, R.A. Billington, et al., Click chemistry reactions in medicinal chemistry:applications of the 1,3-dipolar cycloaddition between azides and alkynes, Med. Res. Rev. 28(2008) 278-308;(c) A. Brik, J. Alexandratos, Y.C. Lin, et al., 2,3-triazole as a peptide surrogate in the rapid synthesis of HIV-1 protease inhibitors, ChemBioChem. 6(2005) 1167-1169.
M Roice, I Johannsen, M Meldal. High capacity poly(ethylene glycol) based amino polymers for peptide and organic synthesis[J]. QSAR Comb. Sci, 2004,23:662-673. doi: 10.1002/(ISSN)1611-0218
S Punna, J Kuzelka, Q Wang, M.G Finn. Head-to-tail peptide cyclodimerization by copper-catalyzed azide-alkyne cycloaddition[J]. Angew. Chem. Int. Ed, 2005,44:2215-2220. doi: 10.1002/(ISSN)1521-3773
R Jagasia, J.M Holub, M Bollinger, K Kirshenbaum, M.G Finn. Peptide cyclization and cyclodimerization by Cu-I-mediated azide-alkyne cycloaddition[J]. J. Org. Chem, 2009,74:2964-2974. doi: 10.1021/jo802097m
B.B Metaferia, M Rittler, J.S Gheeya. Synthesis of novel cyclic NGR/RGD peptide analogs via on resin click chemistry[J]. Bioorg. Med. Chem. Lett, 2010,20:7337-7340. doi: 10.1016/j.bmcl.2010.10.064
S.Y Qin, X.D Xu, C.S Chen. Supramolecular architectures self-assembled from asymmetrical hetero cyclopeptides[J]. Macromol. Rapid Comm, 2011,32:758-764. doi: 10.1002/marc.v32.9/10
V Goncalves, B Gautier, A Regazzetti. On-resin cyclization of peptide ligands of the Vascular Endothelial Growth Factor Receptor 1 by copper(I)-catalyzed 1, 3-dipolar azide-alkyne cycloaddition[J]. Bioorg. Med. Chem. Lett, 2007,17:5590-5594. doi: 10.1016/j.bmcl.2007.07.087
R.A Turner, A.G Oliver, R.S Lokey. Click chemistry as a macrocyclization tool in the solid-phase synthesis of small cyclic peptides[J]. Org. Lett, 2007,9:5011-5014. doi: 10.1021/ol702228u
S Ingale, P.E Dawson. On resin side-chain cyclization of complex peptides using CuAAC[J]. Org. Lett, 2011,13:2822-2825. doi: 10.1021/ol200775h
(a) P.M. Kharkar, M.S. Rehmann, K.M. Skeens, E. Maverakis, A.M. Kloxin, Thiol-ene click hydrogels for therapeutic delivery, ACS Biomater. Sci. Eng. 2(2016) 165-179;(b) J.C. Grim, I.A. Marozas, K.S. Anseth, Thiol-ene and photo-cleavage chemistry for controlled presentation of biomolecules in hydrogels, J. Control. Release. 219(2015) 95-106;(c) H. Chen, Z.L. Zou, S.L. Tan, et al., Efficient synthesis of water-soluble calix[4]-arenes via thiol-ene "click" chemistry, Chin. Chem. Lett. 24(2013) 367-369;(d) Z.L. Yang, Q.Y. Chen, D. Zhou, Y.L. Bu, Synthesis of functional polymer materials via thiol-ene/yne click chemistry, Prog. Chem. 24(2012) 395-404;(e) M.V. Walter, M. Malkoch, Simplifying the synthesis of dendrimers:accelerated approaches, Chem. Soc. Rev 41(2012) 4593-4609;(f) Q. Liu, Q.Y. Zhang, S.J. Chen, J. Zhou, X.F. Lei, Progress in thiol-ene/yne click chemistry, Chin. J. Org. Chem. 32(2012) 1846-1863;(g) G. Franc, A.K. Kakkar, "Click" methodologies:efficient, simple and greener routes to design dendrimers, Chem. Soc. Rev 39(2010) 1536-1544;(h) M. van Dijk, D.T.S. Rijkers, R.M.J. Liskamp, C.F. van Nostrum, W.E. Hennink, Synthesis and applications of biomedical and pharmaceutical polymers via click chemistry methodologies, Bioconjugate Chem. 20(2009) 2001-2016.
A.A Aimetti, R.K Shoemaker, C.C Lin, K.S Anseth. On-resin peptide macrocyclization using thiol-ene click chemistry[J]. Chem. Commun, 2010,46:4061-4063. doi: 10.1039/c001375g
A.A Aimetti, K.R Feaver, K.S Anseth. Synthesis of cyclic, multivalent Arg-Gly-Asp using sequential thiol-ene/thiol-yne photoreactions[J]. Chem. Commun, 2010,46:5781-5783. doi: 10.1039/c0cc01292k
G.C Vougioukalakis, R.H Grubbs. Ruthenium-based heterocyclic carbene-coordinated olefin metathesis catalysts[J]. Chem. Rev, 2010,110:1746-1787. doi: 10.1021/cr9002424
D.T.S. Rijkers, Synthesis of cyclic peptides and peptidomimetics by metathesis reactions, in:Top Heterocycl. Chem., Springer, Berlin Heidelberg, 2015, pp. 1-54.
(a) A.C. Ross, H.Q. Liu, V.R. Pattabiraman, J.C. Vederas, Synthesis of the lantibiotic lactocin S using peptide cyclizations on solid phase, J. Am. Chem. Soc. 132(2010) 462-463;(b) V.R. Pattabiraman, J.L. Stymiest, D.J. Derksen, N.I. Martin, J.C. Vederas, Multiple on-resin olefin metathesis to form ring-expanded analogues of the lantibiotic peptide lacticin 3147 A2, Org. Lett. 9(2007) 699-702.
(a) G.J. Hilinski, Y.W. Kim, J. Hong, et al., Stitched a-helical peptides via bis ringclosing metathesis, J. Am. Chem. Soc. 136(2014) 12314-12322;(b) Y.W. Kim, P.S. Kutchukian, G.L. Verdine, Introduction of all-hydrocarbon i,i +3 staples into alpha-helices via ring-closing olefin metathesis, Org. Lett. 12(2010) 3046-3049.
F Liu, A Giubellino, P.C Simister. Application of ring-closing metathesis to Grb2 SH3 domain-binding peptides[J]. Biopolymers, 2011,96:780-788. doi: 10.1002/bip.v96.6
R Kowalczyk, P.W.R Harris, M.A Brimble. Synthesis and evaluation of disulfide bond mimetics of amylin-(1-8) as agents to treat osteoporosis[J]. Bioorg. Med. Chem, 2012,20:2661-2668. doi: 10.1016/j.bmc.2012.02.030
W.J Fang, Y.J Cui, T.F Murray, J.V Aldrich. Design, synthesis, and pharmacological activities of dynorphin A analogues cyclized by ring-closing metathesis[J]. J. Med. Chem, 2009,52:5619-5625. doi: 10.1021/jm900577k
(a) Y.B. Feng, K. Burgess, Resin effects in solid phase SNAr and SN2 macrocyclizations, Biotechnol. Bioeng 71(2000) 3-8;(b) Y.B. Feng, Z.C. Wang, S. Jin, K. Burgess, SNAr cyclizations to form cyclic peptidomimetics of beta-turns, J. Am. Chem. Soc. 120(1998) 10768-10769;(c) H.B. Lee, M.C. Zaccaro, M. Pattarawarapan, et al., Syntheses and activities of new C-10 b-turn peptidomimetics, J. Org. Chem. 69(2004) 701-713.
E.A Jefferson, S Arakawa, L.B Blyn. New inhibitors of bacterial protein synthesis from a combinatorial library of macrocycles[J]. J. Med. Chem, 2002,45:3430-3439. doi: 10.1021/jm010437x
E.A Jefferson, E.E Swayze, S.A Osgood. Antibacterial activity of quinolone-macrocycle conjugates[J]. Bioorg. Med. Chem. Lett, 2003,13:1635-1638. doi: 10.1016/S0960-894X(03)00285-3
M Giulianotti, A Nefzi. Efficient approach for the diversity-oriented synthesis of macro-heterocycles on solid-support[J]. Tetrahedron Lett, 2003,44:5307-5309. doi: 10.1016/S0040-4039(03)01219-X
Y.B Feng, M Pattarawarapan, Z.C Wang, K Burgess. Solid-phase SN2 macrocyclization reactions to form beta-turn mimics[J]. Org. Lett, 1999,1:121-124. doi: 10.1021/ol990597r
S Derbel, K Ghedira, A Nefzi. Parallel synthesis of 19-membered ring macroheterocycles via intramolecular thioether formation[J]. Tetrahedron Lett, 2010,51:3607-3609. doi: 10.1016/j.tetlet.2010.05.029
P.J Kaniraj, G Maayan. A facile strategy for the construction of cyclic peptoids under microwave irradiation through a simple substitution reaction,[J]. Org. Lett, 2015,17:2110-2113. doi: 10.1021/acs.orglett.5b00696
M Hiroshige, J.R Hauske, P Zhou. Palladium-mediated macrocyclization on solid support and its applications to combinatorial synthesis[J]. J. Am. Chem. Soc, 1995,117:11590-11591. doi: 10.1021/ja00151a029
(a) K. Akaji, K. Teruya, M. Akaji, S. Aimoto, Synthesis of cyclic RGD derivatives via solid phase macrocyclization using the Heck reaction, Tetrahedron 57(2001) 2293-2303;(b) K. Akaji, Y. Kiso, Macrocyclization on solid support using heck reaction, Tetrahedron Lett. 38(1997) 5185-5188.
G Byk, M Cohen-Ohana, D Raichman. Fast and versatile microwave-assisted intramolecular heck reaction in peptide macrocyclization using microwave energy[J]. Biopolymers, 2006,84:274-282. doi: 10.1002/bip.v84:3
A.C Spivey, J McKendrick, R Srikaran, B.A Helm. Solid-phase synthesis of an A-B loop mimetic of the C epsilon 3 domain of human IgE:macrocyclization by sonogashira coupling[J]. J. Org. Chem, 2003,68:1843-1851. doi: 10.1021/jo026693e
A Afonso, L Feliu, M Planas. Solid-phase synthesis of biaryl cyclic peptides by borylation and microwave-assisted intramolecular suzuki-miyaura reaction[J]. Tetrahedron, 2011,67:2238-2245. doi: 10.1016/j.tet.2011.01.084
A Afonso, O Cusso, L Feliu, M Planas. Solid-phase synthesis of biaryl cyclic peptides containing a 3-aryltyrosine[J]. Eur. J. Org. Chem, 2012,31:6204-6211.
Chunhua Ma , Mengjiao Liu , Siyu Ouyang , Zhenwei Cui , Jingjing Bi , Yuqin Jiang , Zhiguo Zhang . Metal-free construction of diverse 1,2,4-triazolo[1,5-a]pyridines on water. Chinese Chemical Letters, 2025, 36(1): 109755-. doi: 10.1016/j.cclet.2024.109755
Yulong Shi , Fenbei Chen , Mengyuan Wu , Xin Zhang , Runze Meng , Kun Wang , Yan Wang , Yuheng Mei , Qionglu Duan , Yinghong Li , Rongmei Gao , Yuhuan Li , Hongbin Deng , Jiandong Jiang , Yanxiang Wang , Danqing Song . Chemical construction and anti-HCoV-OC43 evaluation of novel 10,12-disubstituted aloperine derivatives as dual cofactor inhibitors of TMPRSS2 and SR-B1. Chinese Chemical Letters, 2024, 35(5): 108792-. doi: 10.1016/j.cclet.2023.108792
Huiju Cao , Lei Shi . sp1-Hybridized linear and cyclic carbon chain. Chinese Chemical Letters, 2025, 36(4): 110466-. doi: 10.1016/j.cclet.2024.110466
Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
Yaping Zhang , Wei Zhou , Mingchun Gao , Tianqi Liu , Bingxin Liu , Chang-Hua Ding , Bin Xu . Oxidative cyclization of allyl compounds and isocyanide: A facile entry to polysubstituted 2-cyanopyrroles. Chinese Chemical Letters, 2024, 35(4): 108836-. doi: 10.1016/j.cclet.2023.108836
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Huimin Luan , Qinming Wu , Jianping Wu , Xiangju Meng , Feng-Shou Xiao . Templates for the synthesis of zeolites. Chinese Journal of Structural Chemistry, 2024, 43(4): 100252-100252. doi: 10.1016/j.cjsc.2024.100252
Hang Wang , Qi Wang , Chuan-De Wu . Continuous synthesis of ammonia. Chinese Journal of Structural Chemistry, 2025, 44(3): 100437-100437. doi: 10.1016/j.cjsc.2024.100437
Zhaojun Liu , Zerui Mu , Chuanbo Gao . Alloy nanocrystals: Synthesis paradigms and implications. Chinese Journal of Structural Chemistry, 2023, 42(11): 100156-100156. doi: 10.1016/j.cjsc.2023.100156
Zhenhao Wang , Yuliang Tang , Ruyu Li , Shuai Tian , Yu Tang , Dehai Li . Bioinspired synthesis of cochlearol B and ganocin A. Chinese Chemical Letters, 2024, 35(7): 109247-. doi: 10.1016/j.cclet.2023.109247
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