Base-Promoted Synthesis of β-Substituted-Tryptophans via a Simple and Convenient Three-Component Condensation of Nickel(II) Glycinate
Abstract
:1. Introduction
2. Results and Discussion
3. Materials and Methods
3.1. General
3.2. Typical Procedure for the Synthesis of Nickel(II) Complex (1)
3.3. General Procedure for the Synthesis of Nickel(II) Complex (4a–n)
3.4. General Procedure for the Synthesis of N-Fmoc-β-Substituted-Tryptophan 5a
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
- Wennemers, H. Asymmetric catalysis with peptides. Chem. Commun. 2011, 47, 12036–12041. [Google Scholar] [CrossRef] [PubMed]
- Davie, E.A.C.; Mennen, S.M.; Xu, Y.J.; Miller, S.J. Asymmetric catalysis mediated by synthetic peptides. Chem. Rev. 2007, 107, 5759–5812. [Google Scholar] [CrossRef] [PubMed]
- Kiick, K.L.; Saxon, E.; Tirrell, D.A.; Bertozzi, C.R. Incorporation of azides into recombinant proteins for chemoselective modification by the Staudinger ligation. Proc. Natl. Acad. Sci. USA 2002, 99, 19–24. [Google Scholar] [CrossRef] [PubMed]
- Fowler, V.G.; Boucher, H.W.; Corey, G.R.; Abrutyn, E.; Karchmer, A.W.; Rupp, M.E.; Levine, D.P.; Chambers, H.F.; Tally, F.P.; Vigliani, G.A.; et al. Daptomycin versus standard therapy for bacteremia and endocarditis caused by staphylococcus aureus. N. Engl. J. Med. 2006, 355, 653–665. [Google Scholar] [CrossRef]
- Khoury, G.A.; Smadbeck, J.; Tamamis, P.; Vandris, A.C.; Kieslich, C.A.; Floudas, C.A. Forcefield_NCAA: Ab initio charge parameters to aid in the discovery and design of therapeutic proteins and peptides with unnatural amino acids and their application to complement inhibitors of the compstatin family. ACS Synth. Biol. 2014, 3, 855–869. [Google Scholar] [CrossRef] [PubMed]
- Bonner, G.G.; Davis, P.; Stropova, D.; Edsall, S.; Yamamura, H.I.; Porreca, F.; Hruby, V.J. Opiate aromatic pharmacophore structure-activity relationships in ctap analogues determined by topographical bias, two-dimensional nmr, and biological activity assays. J. Med. Chem. 2000, 43, 569–580. [Google Scholar] [CrossRef] [PubMed]
- Haskellluevano, C.; Toth, K.; Boteju, L.; Job, C.; Castrucci, A.M.D.; Hadley, M.E.; Hruby, V.J. β-Methylation of the phe(7) and trp(9) melanotropin side chain pharmacophores affects ligand-receptor interactions and prolonged biological activity. J. Med. Chem. 1997, 40, 2740–2749. [Google Scholar] [CrossRef] [PubMed]
- Haskellluevano, C.; Boteju, L.W.; Miwa, H.; Dickinson, C.; Gantz, I.; Yamada, T.; Hadley, M.E.; Hruby, V.J. Topographical modification of melanotropin peptide analogs with β-methyltryptophan isomers at position-9 leads to differential potencies and prolonged biological-activities. J. Med. Chem. 1995, 38, 4720–4729. [Google Scholar] [CrossRef]
- Feng, Y.Q.; Chen, G. Total synthesis of celogentin c by stereoselective c-h activation. Angew. Chem. Int. Ed. 2010, 49, 958–961. [Google Scholar] [CrossRef] [PubMed]
- He, L.W.; Yang, L.P.; Castle, S.L. Synthesis of the celogentin c right-hand ring. Org. Lett. 2006, 8, 1165–1168. [Google Scholar] [CrossRef] [PubMed]
- Kobayashi, J.; Suzuki, H.; Shimbo, K.; Takeya, K.; Morita, H. Celogentins a–c, new antimitotic bicyclic peptides from the seeds of Celosia argentea. J. Org. Chem. 2001, 66, 6626–6633. [Google Scholar] [CrossRef] [PubMed]
- Ma, B.; Litvinov, D.N.; He, L.W.; Banerjee, B.; Castle, S.L. Total synthesis of celogentin c. Angew. Chem. Int. Ed. 2009, 48, 6104–6107. [Google Scholar] [CrossRef] [PubMed]
- Ma, B.; Banerjee, B.; Litvinov, D.N.; He, L.W.; Castle, S.L. Total synthesis of the antimitotic bicyclic peptide celogentin c. J. Am. Chem. Soc. 2010, 132, 1159–1171. [Google Scholar] [CrossRef]
- Hu, W.M.; Zhang, F.Y.; Xu, Z.R.; Liu, Q.; Cui, Y.X.; Jia, Y.X. Stereocontrolled and efficient total synthesis of (−)-stephanotic acid methyl ester and (−)-celogentin c. Org. Lett. 2010, 12, 956–959. [Google Scholar] [CrossRef] [PubMed]
- Bentley, D.J.; Slawin, A.M.Z.; Moody, C.J. Total synthesis of stephanotic acid methyl ester. Org. Lett. 2006, 8, 1975–1978. [Google Scholar] [CrossRef] [PubMed]
- Yoshikawa, K.; Tao, S.; Arihara, S. Stephanotic acid, a novel cyclic pentapeptide from the stem of Stephanotis floribunda. J. Nat. Prod. 2000, 63, 540–542. [Google Scholar] [CrossRef] [PubMed]
- Vedejs, E.; Kongkittingam, C. A total synthesis of (−)-hemiasterlin using n-bts methodology. J. Org. Chem. 2001, 66, 7355–7364. [Google Scholar] [CrossRef]
- Zask, A.; Kaplan, J.; Musto, S.; Loganzo, F. Hybrids of the hemiasterlin analogue taltobulin and the dolastatins are potent antimicrotubule agents. J. Am. Chem. Soc. 2005, 127, 17667–17671. [Google Scholar] [CrossRef] [PubMed]
- Chevallier, C.; Richardson, A.D.; Edler, M.C.; Hamel, E.; Harper, M.K.; Ireland, C.M. A new cytotoxic and tubulin-interactive milnamide derivative from a marine sponge Cymbastela sp. Org. Lett. 2003, 5, 3737–3739. [Google Scholar] [CrossRef] [PubMed]
- Liu, C.M.; Masuno, M.N.; MacMillan, J.B.; Molinski, T.F. Enantioselective total synthesis of (+)-milnamide a and evidence of its autoxidation to (+)-milnamide d. Angew. Chem. Int. Ed. 2004, 43, 5951–5954. [Google Scholar] [CrossRef] [PubMed]
- Sonnenschein, R.N.; Farias, J.J.; Tenney, K.; Mooberry, S.L.; Lobkovsky, E.; Clardy, J.; Crews, P. A further study of the cytotoxic constituents of a milnamide-producing sponge. Org. Lett. 2004, 6, 779–782. [Google Scholar] [CrossRef] [PubMed]
- Zheng, B.H.; Ding, C.H.; Hou, X.L.; Dai, L.X. Ag-catalyzed diastereo- and enantioselective synthesis of beta-substituted tryptophans from sulfonylindoles. Org. Lett. 2010, 12, 1688–1691. [Google Scholar] [CrossRef] [PubMed]
- Wang, J.; Zhou, S.B.; Lin, D.Z.; Ding, X.; Jiang, H.L.; Liu, H. Highly diastereo- and enantioselective synthesis of syn-β-substituted tryptophans via asymmetric michael addition of a chiral equivalent of nucleophilic glycine and sulfonylindoles. Chem. Commun. 2011, 47, 8355–8357. [Google Scholar] [CrossRef] [PubMed]
- Herger, M.; van Roye, P.; Romney, D.K.; Brinkmann-Chen, S.; Buller, A.R.; Arnold, F.H. Synthesis of β-branched tryptophan analogues using an engineered subunit of tryptophan synthase. J. Am. Chem. Soc. 2016, 138, 8388–8391. [Google Scholar] [CrossRef] [PubMed]
- Najda, E.; Zakaszewska, A.; Janikowska, K.; Makowiec, S. Practical method for the preparation of 2,2-dimethyl-5-{aryl[(hetero)aryl] methyl}-1,3-dioxane-4,6-diones:Synthesis and mechanistic study. Synthesis-Stuttgart 2016, 48, 3589–3596. [Google Scholar]
- He, Y.H.; Cao, J.F.; Li, R.; Xiang, Y.; Yang, D.C.; Guan, Z. L-Proline-catalyzed multicomponent synthesis of 3-indole derivatives. Tetrahedron 2015, 71, 9299–9306. [Google Scholar] [CrossRef]
- Renzetti, A.; Boffa, E.; Colazzo, M.; Gerard, S.; Sapi, J.; Chan, T.H.; Nakazawa, H.; Villani, C.; Fontana, A. Yonemitsu-type condensations catalysed by proline and eu(otf)(3). RSC Adv. 2014, 4, 47992–47999. [Google Scholar] [CrossRef]
- Dandia, A.; Gupta, S.L.; Parewa, V.; Sharma, A.; Rathore, K.S.; Sharma, A. “On-water” synthesis of 3-substituted indoles via Knoevenagel/Michael addition sequence catalyzed by Cu doped ZnS NPs. Tetrahedron. Lett. 2013, 54, 5711–5717. [Google Scholar] [CrossRef]
- Cochard, F.; Sapi, J.; Laronze, J.Y. A novel and convenient access to highly substituted spiro[pyrrolidinon-3,3′-indoles]. Tetrahedron. Lett. 2001, 42, 6291–6294. [Google Scholar] [CrossRef]
- Shen, Z.L.; Ji, S.J.; Wang, S.Y.; Zeng, X.F. A novel base-promoted synthesis of β-indolylketones via a three-component condensation under ultrasonic irradiation. Tetrahedron 2005, 61, 10552–10558. [Google Scholar] [CrossRef]
- Kawashima, A.; Shu, S.J.; Takeda, R.; Kawamura, A.; Sato, T.; Moriwaki, H.; Wang, J.; Izawa, K.; Acena, J.L.; Soloshonok, V.A.; et al. Advanced asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid by alkylation/cyclization of newly designed axially chiral ni(ii) complex of glycine schiff base. Amino Acids 2016, 48, 973–986. [Google Scholar] [CrossRef] [PubMed]
- Nian, Y.; Wang, J.; Zhou, S.B.; Dai, W.H.; Wang, S.N.; Moriwaki, H.; Kawashima, A.; Soloshonok, V.A.; Liu, H. Purely chemical approach for preparation of d-α-amino acids via (S)-to-(R)-interconversion of unprotected tailor-made α-amino acids. J. Org. Chem. 2016, 81, 3501–3508. [Google Scholar] [CrossRef] [PubMed]
- Li, T.T.; Zhou, S.B.; Wang, J.; Acena, J.L.; Soloshonok, V.A.; Liu, H. Asymmetric synthesis of (2S,3S)-α-(1-oxoisoindolin-3-yl)glycines under low-basicity “kinetic” control. J. Org. Chem. 2015, 80, 11275–11280. [Google Scholar] [CrossRef] [PubMed]
- Li, T.T.; Zhou, S.B.; Wang, J.; Acena, J.L.; Soloshonok, V.A.; Liu, H. Asymmetric synthesis of α-(1-oxoisoindolin-3-yl)glycine: Synthetic and mechanistic challenges. Chem. Commun. 2015, 51, 1624–1626. [Google Scholar] [CrossRef] [PubMed]
- Jorres, M.; Chen, X.; Acena, J.L.; Merkens, C.; Bolm, C.; Liu, H.; Soloshonok, V.A. Asymmetric synthesis of α-amino acids under operationally convenient conditions. Adv. Synth. Catal. 2014, 356, 2203–2208. [Google Scholar] [CrossRef]
- Takeda, R.; Kawamura, A.; Kawashima, A.; Sato, T.; Moriwaki, H.; Izawa, K.; Akaji, K.; Wang, S.N.; Liu, H.; Acena, J.L.; et al. Chemical dynamic kinetic resolution and s/r interconversion of unprotected α-amino acids. Angew. Chem. Int. Ed. 2014, 53, 12214–12217. [Google Scholar] [CrossRef] [PubMed]
- Zhou, S.B.; Wang, J.; Chen, X.; Acena, J.L.; Soloshonok, V.A.; Liu, H. Chemical kinetic resolution of unprotected β-substituted β-amino acids using recyclable chiral ligands. Angew. Chem. Int. Ed. 2014, 53, 7883–7886. [Google Scholar] [CrossRef] [PubMed]
- Lin, D.Z.; Wang, J.; Zhang, X.; Zhou, S.B.; Lian, J.; Jiang, H.L.; Liu, H. Highly diastereoselective synthesis of 3-indolylglycines via an asymmetric oxidative heterocoupling reaction of a chiral nickel(II) complex and indoles. Chem. Commun. 2013, 49, 2575–2577. [Google Scholar] [CrossRef] [PubMed]
- Youm, I.; Musazzi, U.M.; Gratton, M.A.; Murowchick, J.B.; Youan, B.B.C. Label-Free ferrocene-loaded nanocarrier engineering for in vivo cochlear drug delivery and imaging. J. Pharm. Sci. 2016, 105, 3162–3171. [Google Scholar] [CrossRef] [PubMed]
- Cevik, E.; Bahar, O.; Senel, M.; Abasiyanik, M.F. Construction of novel electrochemical immunosensor for detection of prostate specific antigen using ferrocene-pamam dendrimers. Biosens. Bioelectron. 2016, 86, 1074–1079. [Google Scholar] [CrossRef] [PubMed]
- Jiang, Q.L.; Zhang, S.; Tian, M.; Zhang, S.Y.; Xie, T.; Chen, D.Y.; Chen, Y.J.; He, J.; Liu, J.; Ouyang, L.; Jiang, X. Plant lectins, from ancient sugar-binding proteins to emerging anti-cancer drugs in apoptosis and autophagy. Cell Prolif. 2015, 48, 17–28. [Google Scholar] [CrossRef]
- Chen, C.; Wang, T.; Wu, F.; Huang, W.; He, G.; Ouyang, L.; Xiang, M.; Peng, C.; Jiang, Q. Combining structure-based pharmacophore modeling, virtual screening, and in silico ADMET analysis to discover novel tetrahydro-quinoline based pyruvate kinase isozyme M2 activators with antitumor activity. Drug Des. Dev. Ther. 2014, 8, 1195–1210. [Google Scholar]
- Ellis, T.K.; Ueki, H.; Soloshonok, V.A. New generation of nucleophilic glycine equivalents. Tetrahedron. Lett. 2005, 46, 941–944. [Google Scholar] [CrossRef]
Sample Availability: Samples of the compounds 4a–4n are available from the authors. |
Entry | Base | Solvent | Temp (°C) | Yield (%) a |
---|---|---|---|---|
1 | NaOH | MeCN | 80 | NR b |
2 | NaOH | EtOH | 80 | 15 |
3 | NaOH | Glycerol | 80 | 28 |
5 | LiOH | Glycerol | 80 | 32 |
6 | DIEA | Glycerol | 80 | NR |
7 | DBU | Glycerol | 80 | 11 |
8 | TMG | Glycerol | 80 | 46 |
9 | TMG | Glycerol | 40 | NR |
10 | TMG | Glycerol | 70 | 57 |
11 | TMG | Glycerol | 90 | 45 |
Entry | Compound | Ar | R1 | R2 | Yield(%) a |
---|---|---|---|---|---|
1 | 4a | Phenyl | H | H | 57 |
2 | 4b | 3-OMe phenyl | H | H | 62 |
3 | 4c | 4-Br phenyl | H | H | 55 |
4 | 4d | 4-tBu phenyl | H | H | 44 |
5 | 4e | 3-Cl phenyl | H | H | 58 |
6 | 4f | 4-CF3 phenyl | H | H | 60 |
7 | 4g | 4-Me phenyl | H | H | 66 |
8 | 4h | 4-NO2 phenyl | H | H | 35 |
9 | 4i | Ferrocene | H | H | 43 |
10 | 4j | Phenyl | H | Me | 45 |
11 | 4k | Phenyl | 4-Br | H | 43 |
12 | 4l | Phenyl | 5-Cl | H | 53 |
13 | 4m | Phenyl | 6-F | H | 57 |
14 | 4n | Phenyl | 7-Me | H | 55 |
15 | 4o | 4-(dimethylamino) phenyl | H | H | NR b |
16 | 4p | 4-Pyridine | H | H | NP c |
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Zhou, R.; Pan, Z.; Zhang, Y.; Wu, F.; Jiang, Q.; Guo, L. Base-Promoted Synthesis of β-Substituted-Tryptophans via a Simple and Convenient Three-Component Condensation of Nickel(II) Glycinate. Molecules 2017, 22, 695. https://doi.org/10.3390/molecules22050695
Zhou R, Pan Z, Zhang Y, Wu F, Jiang Q, Guo L. Base-Promoted Synthesis of β-Substituted-Tryptophans via a Simple and Convenient Three-Component Condensation of Nickel(II) Glycinate. Molecules. 2017; 22(5):695. https://doi.org/10.3390/molecules22050695
Chicago/Turabian StyleZhou, Rui, Zhaoping Pan, Yuehua Zhang, Fengbo Wu, Qinglin Jiang, and Li Guo. 2017. "Base-Promoted Synthesis of β-Substituted-Tryptophans via a Simple and Convenient Three-Component Condensation of Nickel(II) Glycinate" Molecules 22, no. 5: 695. https://doi.org/10.3390/molecules22050695