메뉴 건너뛰기




Volumn 3, Issue 12, 2017, Pages

Direct N-alkylation of unprotected amino acids with alcohols

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; ALKYLATION; AMINO ACIDS;

EID: 85041913080     PISSN: None     EISSN: 23752548     Source Type: Journal    
DOI: 10.1126/sciadv.aao6494     Document Type: Article
Times cited : (79)

References (45)
  • 1
    • 84984622717 scopus 로고    scopus 로고
    • Oxidative diversification of amino acids and peptides by small-molecule iron catalysis
    • T. J. Osberger, D. C. Rogness, J. T. Kohrt, A. F. Stepan, M. C. White, Oxidative diversification of amino acids and peptides by small-molecule iron catalysis. Nature 537, 214–219 (2016).
    • (2016) Nature , vol.537 , pp. 214-219
    • Osberger, T.J.1    Rogness, D.C.2    Kohrt, J.T.3    Stepan, A.F.4    White, M.C.5
  • 3
    • 84862760493 scopus 로고    scopus 로고
    • Availability of protein-derived amino acids as feedstock for the production of bio-based chemicals
    • T. M. Lammens, M. C. R. Franssen, E. L. Scott, J. P. M. Sanders, Availability of protein-derived amino acids as feedstock for the production of bio-based chemicals. Biomass Bioenergy 44, 168–181 (2012).
    • (2012) Biomass Bioenergy , vol.44 , pp. 168-181
    • Lammens, T.M.1    Franssen, M.C.R.2    Scott, E.L.3    Sanders, J.P.M.4
  • 4
    • 35448951406 scopus 로고    scopus 로고
    • Nonclinical safety evaluation of muraglitazar, a novel PPARa/g agonist
    • C. R. Waites, M. A. Dominick, T. P. Sanderson, B. E. Schilling, Nonclinical safety evaluation of muraglitazar, a novel PPARa/g agonist. Toxicol. Sci. 100, 248–258 (2007).
    • (2007) Toxicol. Sci. , vol.100 , pp. 248-258
    • Waites, C.R.1    Dominick, M.A.2    Sanderson, T.P.3    Schilling, B.E.4
  • 5
    • 81255152303 scopus 로고    scopus 로고
    • Selective N-alkylation of b-alanine facilitates the synthesis of a poly(amino acid)-based theranostic nanoagent
    • S. Santra, J. M. Perez, Selective N-alkylation of b-alanine facilitates the synthesis of a poly(amino acid)-based theranostic nanoagent. Biomacromolecules 12, 3917–3927 (2011).
    • (2011) Biomacromolecules , vol.12 , pp. 3917-3927
    • Santra, S.1    Perez, J.M.2
  • 8
    • 0001164654 scopus 로고    scopus 로고
    • Efficient and highly selective copper(II) transport across a bulk liquid chloroform membrane mediated by lipophilic dipeptides
    • M. C. Cleij, P. Scrimin, P. Tecilla, U. Tonellato, Efficient and highly selective copper(II) transport across a bulk liquid chloroform membrane mediated by lipophilic dipeptides. J. Org. Chem. 62, 5592–5599 (1997).
    • (1997) J. Org. Chem. , vol.62 , pp. 5592-5599
    • Cleij, M.C.1    Scrimin, P.2    Tecilla, P.3    Tonellato, U.4
  • 9
    • 84873279753 scopus 로고    scopus 로고
    • Metal complex catalysis in living biological systems
    • P. K. Sasmal, C. N. Streu, E. Meggers, Metal complex catalysis in living biological systems. Chem. Commun. 49, 1581–1587 (2013).
    • (2013) Chem. Commun. , vol.49 , pp. 1581-1587
    • Sasmal, P.K.1    Streu, C.N.2    Meggers, E.3
  • 10
  • 15
    • 84901248068 scopus 로고    scopus 로고
    • Catalytic conversion of nonfood woody biomass solids to organic liquids
    • K. Barta, P. C. Ford, Catalytic conversion of nonfood woody biomass solids to organic liquids. Acc. Chem. Res. 47, 1503–1512 (2014).
    • (2014) Acc. Chem. Res. , vol.47 , pp. 1503-1512
    • Barta, K.1    Ford, P.C.2
  • 18
    • 84880418740 scopus 로고    scopus 로고
    • Applications of acceptorless dehydrogenation and related transformations in chemical synthesis
    • C. Gunanathan, D. Milstein, Applications of acceptorless dehydrogenation and related transformations in chemical synthesis. Science 341, 1229712 (2013).
    • (2013) Science , vol.341 , pp. 1229712
    • Gunanathan, C.1    Milstein, D.2
  • 20
    • 77957836901 scopus 로고    scopus 로고
    • Efficient and chemoselective alkylation of amines/amino acids using alcohols as alkylating reagents under mild conditions
    • C.-P. Xu, Z.-H. Xiao, B.-Q. Zhuo, Y.-H. Wang, P.-Q. Huang, Efficient and chemoselective alkylation of amines/amino acids using alcohols as alkylating reagents under mild conditions. Chem. Commun. 46, 7834–7836 (2010).
    • (2010) Chem. Commun. , vol.46 , pp. 7834-7836
    • Xu, C.-P.1    Xiao, Z.-H.2    Zhuo, B.-Q.3    Wang, Y.-H.4    Huang, P.-Q.5
  • 21
    • 79956287012 scopus 로고    scopus 로고
    • Palladium-catalyzed mono-N-allylation of unprotected amino acids with 1,1-dimethylallyl alcohol in water
    • H. Hikawa, Y. Yokoyama, Palladium-catalyzed mono-N-allylation of unprotected amino acids with 1,1-dimethylallyl alcohol in water. Org. Biomol. Chem. 9, 4044–4050 (2011).
    • (2011) Org. Biomol. Chem. , vol.9 , pp. 4044-4050
    • Hikawa, H.1    Yokoyama, Y.2
  • 22
    • 33845375188 scopus 로고
    • A new group of ruthenium complexes: Structure and catalysis
    • Y. Shvo, D. Czarkie, Y. Rahamim, D. F. Chodosh, A new group of ruthenium complexes: Structure and catalysis. J. Am. Chem. Soc. 108, 7400–7402 (1986).
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 7400-7402
    • Shvo, Y.1    Czarkie, D.2    Rahamim, Y.3    Chodosh, D.F.4
  • 23
    • 77951241253 scopus 로고    scopus 로고
    • Discovery, applications, and catalytic mechanisms of Shvo’s catalyst
    • B. L. Conley, M. K. Pennington-Boggio, E. Boz, T. J. Williams, Discovery, applications, and catalytic mechanisms of Shvo’s catalyst. Chem. Rev. 110, 2294–2312 (2010).
    • (2010) Chem. Rev. , vol.110 , pp. 2294-2312
    • Conley, B.L.1    Pennington-Boggio, M.K.2    Boz, E.3    Williams, T.J.4
  • 24
    • 80051982377 scopus 로고    scopus 로고
    • 2(amidine)] effectively catalyze the formation of tertiary amines from the reaction of primary alcohols and ammonium salts
    • 2(amidine)] effectively catalyze the formation of tertiary amines from the reaction of primary alcohols and ammonium salts. Adv. Synth. Catal. 353, 2078–2084 (2011).
    • (2011) Adv. Synth. Catal. , vol.353 , pp. 2078-2084
    • Segarra, C.1    Mas-Marzá, E.2    Mata, J.A.3    Peris, E.4
  • 25
    • 13644254490 scopus 로고    scopus 로고
    • Isomerization and deuterium scrambling evidence for a change in the rate-limiting step during imine hydrogenation by Shvo’s hydroxycyclopentadienyl ruthenium hydride
    • C. P. Casey, J. B. Johnson, Isomerization and deuterium scrambling evidence for a change in the rate-limiting step during imine hydrogenation by Shvo’s hydroxycyclopentadienyl ruthenium hydride. J. Am. Chem. Soc. 127, 1883–1894 (2005).
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 1883-1894
    • Casey, C.P.1    Johnson, J.B.2
  • 26
    • 36049019584 scopus 로고    scopus 로고
    • A general ruthenium-catalyzed synthesis of aromatic amines
    • D. Hollmann, S. Bähn, A. Tillack, M. Beller, A general ruthenium-catalyzed synthesis of aromatic amines. Angew. Chem. Int. Ed. 46, 8291–8294 (2007).
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 8291-8294
    • Hollmann, D.1    Bähn, S.2    Tillack, A.3    Beller, M.4
  • 27
    • 84918498938 scopus 로고    scopus 로고
    • Selective chemical protein modification
    • C. D. Spicer, B. G. Davis, Selective chemical protein modification. Nat. Commun. 5, 4740 (2014).
    • (2014) Nat. Commun. , vol.5 , pp. 4740
    • Spicer, C.D.1    Davis, B.G.2
  • 28
    • 84909619767 scopus 로고    scopus 로고
    • Protein amino-terminal modifications and proteomic approaches for N-terminal profiling
    • Z. W. Lai, A. Petrera, O. Schilling, Protein amino-terminal modifications and proteomic approaches for N-terminal profiling. Curr. Opin. Chem. Biol. 24, 71–79 (2015).
    • (2015) Curr. Opin. Chem. Biol. , vol.24 , pp. 71-79
    • Lai, Z.W.1    Petrera, A.2    Schilling, O.3
  • 29
    • 84939000784 scopus 로고    scopus 로고
    • Amino acid-based surfactants—Do they deserve more attention?
    • R. Bordes, K. Holmberg, Amino acid-based surfactants—Do they deserve more attention? Adv. Colloid Interface Sci. 222, 79–91 (2015).
    • (2015) Adv. Colloid Interface Sci. , vol.222 , pp. 79-91
    • Bordes, R.1    Holmberg, K.2
  • 30
    • 84923330616 scopus 로고    scopus 로고
    • Iron catalysed direct alkylation of amines with alcohols
    • T. Yan, B. L. Feringa, K. Barta, Iron catalysed direct alkylation of amines with alcohols. Nat. Commun. 5, 5602 (2014).
    • (2014) Nat. Commun. , vol.5 , pp. 5602
    • Yan, T.1    Feringa, B.L.2    Barta, K.3
  • 31
    • 84953319096 scopus 로고    scopus 로고
    • Benzylamines via iron-catalyzed direct amination of benzyl alcohols
    • T. Yan, B. L. Feringa, K. Barta, Benzylamines via iron-catalyzed direct amination of benzyl alcohols. ACS Catal. 6, 381–388 (2016).
    • (2016) ACS Catal. , vol.6 , pp. 381-388
    • Yan, T.1    Feringa, B.L.2    Barta, K.3
  • 32
    • 84863274593 scopus 로고    scopus 로고
    • Air-stable, nitrile-ligated (cyclopentadienone) iron dicarbonyl compounds as transfer reduction and oxidation catalysts
    • T. N. Plank, J. L. Drake, D. K. Kim, T. W. Funk, Air-stable, nitrile-ligated (cyclopentadienone) iron dicarbonyl compounds as transfer reduction and oxidation catalysts. Adv. Synth. Catal. 354, 597–601 (2012).
    • (2012) Adv. Synth. Catal. , vol.354 , pp. 597-601
    • Plank, T.N.1    Drake, J.L.2    Kim, D.K.3    Funk, T.W.4
  • 33
    • 0036042072 scopus 로고    scopus 로고
    • Sodium borohydride: A versatile reagent in the reductive N-monoalkylation of a-amino acids and a-amino methyl esters
    • G. Verardo, P. Geatti, E. Pol, A. G. Giumanini, Sodium borohydride: A versatile reagent in the reductive N-monoalkylation of a-amino acids and a-amino methyl esters. Can. J. Chem. 80, 779–788 (2002).
    • (2002) Can. J. Chem. , vol.80 , pp. 779-788
    • Verardo, G.1    Geatti, P.2    Pol, E.3    Giumanini, A.G.4
  • 39
    • 0035043529 scopus 로고    scopus 로고
    • Scope and limitation of the acid-catalyzed isomerization of Aib-containing thiopeptides
    • R. A. Breitenmoser, H. Heimgartner, Scope and limitation of the acid-catalyzed isomerization of Aib-containing thiopeptides. Helv. Chim. Acta 84, 786–796 (2001).
    • (2001) Helv. Chim. Acta , vol.84 , pp. 786-796
    • Breitenmoser, R.A.1    Heimgartner, H.2
  • 41
    • 77955344644 scopus 로고    scopus 로고
    • Pairing fullerenes and porphyrins: Supramolecular wires that exhibit charge transfer activity
    • F. Wessendorf, B. Grimm, D. M. Guldi, A. Hirsch, Pairing fullerenes and porphyrins: Supramolecular wires that exhibit charge transfer activity. J. Am. Chem. Soc. 132, 10786–10795 (2010).
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 10786-10795
    • Wessendorf, F.1    Grimm, B.2    Guldi, D.M.3    Hirsch, A.4
  • 43
    • 70349277032 scopus 로고    scopus 로고
    • COMU: A safer and more effective replacement for benzotriazole-based uronium coupling reagents
    • A. El-Faham, R. S. Funosas, R. Prohens, F. Albericio, COMU: A safer and more effective replacement for benzotriazole-based uronium coupling reagents. Chemistry 15, 9404–9416 (2009).
    • (2009) Chemistry , vol.15 , pp. 9404-9416
    • El-Faham, A.1    Funosas, R.S.2    Prohens, R.3    Albericio, F.4
  • 44
    • 4344705327 scopus 로고    scopus 로고
    • Trimethylsilyldiazomethane—A mild and efficient reagent for the methylation of carboxylic acids and alcohols in natural products
    • A. Presser, A. Hüfner, Trimethylsilyldiazomethane—A mild and efficient reagent for the methylation of carboxylic acids and alcohols in natural products. Monatsh. Chem. 135, 1015–1022 (2004).
    • (2004) Monatsh. Chem. , vol.135 , pp. 1015-1022
    • Presser, A.1    Hüfner, A.2
  • 45
    • 84869384193 scopus 로고    scopus 로고
    • Copper-catalyzed amination of ketene silyl acetals with hydroxylamines: Electrophilic amination approach to a-amino acids
    • N. Matsuda, K. Hirano, T. Satoh, M. Miura, Copper-catalyzed amination of ketene silyl acetals with hydroxylamines: Electrophilic amination approach to a-amino acids. Angew. Chem. Int. Ed. 51, 11827–11831 (2012).
    • (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 11827-11831
    • Matsuda, N.1    Hirano, K.2    Satoh, T.3    Miura, M.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.