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Volumn 16, Issue 10, 2010, Pages 563-567

Phosphoramidate-peptide synthesis by solution- and solid-phase Staudinger-phosphite reactions

Author keywords

Aryl azides; Chemoselective reaction; Phosphoramidate; Solid supported reaction; Staudinger phosphite reaction

Indexed keywords

PEPTIDE DERIVATIVE; PHOSPHITE; PHOSPHORAMIDIC ACID DERIVATIVE;

EID: 78149386472     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.1236     Document Type: Article
Times cited : (12)

References (34)
  • 1
    • 24044531286 scopus 로고    scopus 로고
    • Organic azides: an exploding diversity of a unique class of compounds
    • Bräse S, Gil C, Knepper K, Zimmermann V. Organic azides: an exploding diversity of a unique class of compounds. Angew. Chem. Int. Ed. 2005; 44: 5188-5240.
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 5188-5240
    • Bräse, S.1    Gil, C.2    Knepper, K.3    Zimmermann, V.4
  • 2
    • 9344227358 scopus 로고    scopus 로고
    • A strain-promoted [3 + 2] azide-alkyne cycloaddition for covalent modification of biomolecules in living systems
    • Agard NJ, Prescher JA, Bertozzi CR. A strain-promoted [3 + 2] azide-alkyne cycloaddition for covalent modification of biomolecules in living systems. J. Am. Chem. Soc. 2004; 126: 15046-15047.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 15046-15047
    • Agard, N.J.1    Prescher, J.A.2    Bertozzi, C.R.3
  • 3
    • 0037099395 scopus 로고    scopus 로고
    • A stepwise Huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes
    • Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. A stepwise Huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes. Angew. Chem. Int. Ed. 2002; 41: 2596-2599.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 2596-2599
    • Rostovtsev, V.V.1    Green, L.G.2    Fokin, V.V.3    Sharpless, K.B.4
  • 4
    • 0034677879 scopus 로고    scopus 로고
    • Cell surface engineering by a modified Staudinger reaction
    • Saxon E, Bertozzi CR. Cell surface engineering by a modified Staudinger reaction. Science. 2000; 287: 2007-2010.
    • (2000) Science , vol.287 , pp. 2007-2010
    • Saxon, E.1    Bertozzi, C.R.2
  • 5
    • 57749121492 scopus 로고    scopus 로고
    • Chemoselective ligation and modification strategies for peptides and proteins
    • Hackenberger CPR, Schwarzer D. Chemoselective ligation and modification strategies for peptides and proteins. Angew. Chem. Int. Ed. 2008; 47: 10030-10074.
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 10030-10074
    • Hackenberger, C.P.R.1    Schwarzer, D.2
  • 6
    • 1042287130 scopus 로고    scopus 로고
    • The development and application of methods for activity-based protein profiling
    • Jessani N, Cravatt BF. The development and application of methods for activity-based protein profiling. Curr. Opin. Chem. Biol. 2004; 8: 54-59.
    • (2004) Curr. Opin. Chem. Biol. , vol.8 , pp. 54-59
    • Jessani, N.1    Cravatt, B.F.2
  • 9
    • 0037012920 scopus 로고    scopus 로고
    • Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides
    • Tornoe CW, Christensen C, Meldal M. Peptidotriazoles on solid phase: [1, 2, 3]-triazoles by regiospecific copper(I)-catalyzed 1, 3-dipolar cycloadditions of terminal alkynes to azides. J. Org. Chem. 2002; 67: 3057-3064.
    • (2002) J. Org. Chem. , vol.67 , pp. 3057-3064
    • Tornoe, C.W.1    Christensen, C.2    Meldal, M.3
  • 10
    • 78149392317 scopus 로고    scopus 로고
    • A new bioorthogonal ligation for labelling of azide-bearing glycoconjugates
    • Agard NJ, Prescher JA, Bertozzi CR. A new bioorthogonal ligation for labelling of azide-bearing glycoconjugates. Glycobiology. 2004; 14: 1197-1197.
    • (2004) Glycobiology , vol.14 , pp. 1197-1197
    • Agard, N.J.1    Prescher, J.A.2    Bertozzi, C.R.3
  • 11
    • 26844534670 scopus 로고    scopus 로고
    • Methyltransferase-directed DNA strand scission
    • Comstock LR, Rajski SR. Methyltransferase-directed DNA strand scission. J. Am. Chem. Soc. 2005; 127: 14136-14137.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 14136-14137
    • Comstock, L.R.1    Rajski, S.R.2
  • 14
    • 0037039298 scopus 로고    scopus 로고
    • Incorporation of azides into recombinant proteins for chemoselective modification by the Staudinger ligation
    • Kiick KL, Saxon E, Tirrell DA, Bertozzi CR. Incorporation of azides into recombinant proteins for chemoselective modification by the Staudinger ligation. Proc. Natl. Acad. Sci. U.S.A. 2002; 99: 19-24.
    • (2002) Proc. Natl. Acad. Sci. U.S.A. , vol.99 , pp. 19-24
    • Kiick, K.L.1    Saxon, E.2    Tirrell, D.A.3    Bertozzi, C.R.4
  • 16
    • 33745464039 scopus 로고    scopus 로고
    • Selective identification of newly synthesized proteins in mammalian cells using bioorthogonal noncanonical amino acid tagging (BONCAT)
    • Dieterich DC, Link AJ, Graumann J, Tirrell DA, Schuman EM. Selective identification of newly synthesized proteins in mammalian cells using bioorthogonal noncanonical amino acid tagging (BONCAT). Proc. Natl. Acad. Sci. U.S.A. 2006; 103: 9482-9487.
    • (2006) Proc. Natl. Acad. Sci. U.S.A. , vol.103 , pp. 9482-9487
    • Dieterich, D.C.1    Link, A.J.2    Graumann, J.3    Tirrell, D.A.4    Schuman, E.M.5
  • 18
  • 21
  • 23
    • 0015130167 scopus 로고
    • Peptide syntheses .51. Antamanide .9. Synthesis of an antitoxic variant of antamanide with P-azidophenylalanine in position 6
    • Wieland T, Dungen AV, Birr C. Peptide syntheses .51. Antamanide .9. Synthesis of an antitoxic variant of antamanide with P-azidophenylalanine in position 6. Liebigs Ann. Chem. 1971; 752: 109-114.
    • (1971) Liebigs Ann. Chem. , vol.752 , pp. 109-114
    • Wieland, T.1    Dungen, A.V.2    Birr, C.3
  • 24
    • 0020320763 scopus 로고
    • Synthesis and biological activities of photoaffinity labeling analogs of substance P
    • Escher E, Couture R, Champagne G, Mizrahi J, Regoli D. Synthesis and biological activities of photoaffinity labeling analogs of substance P. J. Med. Chem. 1982; 25: 470-475.
    • (1982) J. Med. Chem. , vol.25 , pp. 470-475
    • Escher, E.1    Couture, R.2    Champagne, G.3    Mizrahi, J.4    Regoli, D.5
  • 25
    • 0018184755 scopus 로고
    • Photoaffinity labeling of angiotensin-II receptor. 1. Synthesis and biological activities of labeling peptides
    • Escher EHF, Nguyen TMD, Robert H, St-pierre SA, Regoli DC. Photoaffinity labeling of angiotensin-II receptor. 1. Synthesis and biological activities of labeling peptides. J. Med. Chem. 1978; 21: 860-864.
    • (1978) J. Med. Chem. , vol.21 , pp. 860-864
    • Escher, E.H.F.1    Nguyen, T.M.D.2    Robert, H.3    St-pierre, S.A.4    Regoli, D.C.5
  • 26
    • 0021088123 scopus 로고
    • [1,6-Alpha-aminosuberic acid, 3-(para-azidophenylalanine), 8-arginine] vasopressin: a new photoaffinity label for hydroosmotic hormone
    • Fahrenholz F, Toth G, Crause P, Eggena P, Schwartz IL. [1, 6-Alpha-aminosuberic acid, 3-(para-azidophenylalanine), 8-arginine] vasopressin: a new photoaffinity label for hydroosmotic hormone. J. Biol. Chem. 1983; 258: 14861-14867.
    • (1983) J. Biol. Chem. , vol.258 , pp. 14861-14867
    • Fahrenholz, F.1    Toth, G.2    Crause, P.3    Eggena, P.4    Schwartz, I.L.5
  • 27
    • 0033615598 scopus 로고    scopus 로고
    • Determination of the binding site on the extracellular domain of guanylyl cyclase C to heat-stable enterotoxin
    • Hasegawa M, Hidaka Y, Matsumoto Y, Sanni T, Shimonishi Y. Determination of the binding site on the extracellular domain of guanylyl cyclase C to heat-stable enterotoxin. J. Biol. Chem. 1999; 274: 31713-31718.
    • (1999) J. Biol. Chem. , vol.274 , pp. 31713-31718
    • Hasegawa, M.1    Hidaka, Y.2    Matsumoto, Y.3    Sanni, T.4    Shimonishi, Y.5
  • 28
    • 0024498359 scopus 로고
    • Synthesis of highly mu-opioid and delta-opioid receptor selective peptides containing a photoaffinity group
    • Landis G, Lui G, Shook JE, Yamamura HI, Burks TF, Hruby VJ. Synthesis of highly mu-opioid and delta-opioid receptor selective peptides containing a photoaffinity group. J. Med. Chem. 1989; 32: 638-643.
    • (1989) J. Med. Chem. , vol.32 , pp. 638-643
    • Landis, G.1    Lui, G.2    Shook, J.E.3    Yamamura, H.I.4    Burks, T.F.5    Hruby, V.J.6
  • 29
    • 0023097616 scopus 로고
    • Synthesis and placental binding potencies of photosensitive analogues of luteinizing-hormone-releasing hormone (Lhrh) with agonistic and antagonistic structures
    • Mackiewicz Z, Belisle S, Bellabarba D, Gallopayet N, Lehoux JG, Lagace G, Escher E. Synthesis and placental binding potencies of photosensitive analogues of luteinizing-hormone-releasing hormone (Lhrh) with agonistic and antagonistic structures. Helv. Chim. Acta 1987; 70: 423-429.
    • (1987) Helv. Chim. Acta , vol.70 , pp. 423-429
    • Mackiewicz, Z.1    Belisle, S.2    Bellabarba, D.3    Gallopayet, N.4    Lehoux, J.G.5    Lagace, G.6    Escher, E.7
  • 30
    • 0024809040 scopus 로고
    • Photoaffinity-labeling of pepsin
    • Yonezawa H, Wada T. Photoaffinity-labeling of pepsin. Bull. Chem. Soc. Jpn. 1989; 62: 3730-3732.
    • (1989) Bull. Chem. Soc. Jpn. , vol.62 , pp. 3730-3732
    • Yonezawa, H.1    Wada, T.2
  • 34
    • 0030669531 scopus 로고    scopus 로고
    • Structurally modified firefly luciferase. Effects of amino acid substitution at position 286
    • Arslan T, Mamaev SV, Mamaeva NV, Hecht SM. Structurally modified firefly luciferase. Effects of amino acid substitution at position 286. J. Am. Chem. Soc. 1997; 119: 10877-10887.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 10877-10887
    • Arslan, T.1    Mamaev, S.V.2    Mamaeva, N.V.3    Hecht, S.M.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.