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Volumn 74, Issue 15, 2009, Pages 5260-5266

N-urethane-protected amino alkyl isothiocyanates: Synthesis, isolation, characterization, and application to the synthesis of thioureidopeptides

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC UNIT; CENTROSYMMETRIC; CHEMICAL EQUATIONS; ISOTHIOCYANATES; NONCENTROSYMMETRIC SPACE GROUPS; ORTHORHOMBIC CRYSTAL SYSTEM; PEPTIDOMIMETICS; SINGLE MOLECULE; SPACE GROUPS;

EID: 68049103235     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900675s     Document Type: Article
Times cited : (42)

References (130)
  • 5
    • 68049114039 scopus 로고    scopus 로고
    • For selected reviews on various types of peptidomimetic synthesis and their biological applications, see: (a) Synthesis of Peptides and & Peptidomimetics Houben-Weyl, Goodman, M, Felix, A, Moroder, L, Toniolo, C, Eds, Georg Thieme Verlag: Stuttgart, Germany, 2003; E22c and references cited therein
    • For selected reviews on various types of peptidomimetic synthesis and their biological applications, see: (a) Synthesis of Peptides and & Peptidomimetics (Houben-Weyl); Goodman, M.; Felix, A.; Moroder, L.; Toniolo, C.; Eds.; Georg Thieme Verlag: Stuttgart, Germany, 2003; Vol. E22c and references cited therein.
  • 8
    • 68049102650 scopus 로고    scopus 로고
    • Peptides: Chemistry and Biology; Sewald, N.; Jakubke, H. -D.; Eds.; Wiley-VCH: Weinheim, Germany, 2002; p 354.
    • (d) Peptides: Chemistry and Biology; Sewald, N.; Jakubke, H. -D.; Eds.; Wiley-VCH: Weinheim, Germany, 2002; p 354.
  • 9
    • 0033550306 scopus 로고    scopus 로고
    • For selected class of peptidomimetics: (i) For ureas see: (a) Guichard, G.; Semetey, V.; Didierjean, C.; Aubry, A.; Briand, J. P.; Rodriguez, M. J. Org. Chem. 1999, 64, 8702-8705.
    • For selected class of peptidomimetics: (i) For ureas see: (a) Guichard, G.; Semetey, V.; Didierjean, C.; Aubry, A.; Briand, J. P.; Rodriguez, M. J. Org. Chem. 1999, 64, 8702-8705.
  • 14
    • 84962436408 scopus 로고    scopus 로고
    • For hydrazino peptides see: f
    • (v) For hydrazino peptides see: (f) Gunther, R.; Hofmann, H. J. J. Am. Chem. Soc. 2001, 123, 247-255.
    • (2001) J. Am. Chem. Soc , vol.123 , pp. 247-255
    • Gunther, R.1    Hofmann, H.J.2
  • 37
    • 0035793285 scopus 로고    scopus 로고
    • and references cited therein
    • (c) Beer, P. D.; Gale, P. Angew. Chem., Int. Ed. 2001, 40, 486-516 and references cited therein.
    • (2001) Angew. Chem., Int. Ed , vol.40 , pp. 486-516
    • Beer, P.D.1    Gale, P.2
  • 41
    • 0003554758 scopus 로고    scopus 로고
    • For the first application of chiral thioureas as organic catalysts, see
    • For the first application of chiral thioureas as organic catalysts, see: Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901-4902.
    • (1998) J. Am. Chem. Soc , vol.120 , pp. 4901-4902
    • Sigman, M.S.1    Jacobsen, E.N.2
  • 42
    • 33746643770 scopus 로고    scopus 로고
    • For the use of thiourea derived from Pro as a catalyst which was prepared by coupling Boc-β-proline amine with 3,5-bis(trifluoromethyl) phenyl isothiocyanate, see: Cao, C. L, Ye, M. C, Sun, X. L, Tang, Y. Org. Lett. 2006, 8, 2901-2904
    • For the use of thiourea derived from Pro as a catalyst which was prepared by coupling Boc-β-proline amine with 3,5-bis(trifluoromethyl) phenyl isothiocyanate, see: Cao, C. L.; Ye, M. C.; Sun, X. L.; Tang, Y. Org. Lett. 2006, 8, 2901-2904.
  • 43
    • 38349135345 scopus 로고    scopus 로고
    • For recent reviews on thioureas as organocatalysts, see: a
    • For recent reviews on thioureas as organocatalysts, see: (a) Doyle, A. G.; Jacobsen, E. N. Chem. Rev. 2007, 107, 5713-5743.
    • (2007) Chem. Rev , vol.107 , pp. 5713-5743
    • Doyle, A.G.1    Jacobsen, E.N.2
  • 61
    • 84055209507 scopus 로고
    • and references cited therein. For a review on organic isothiocyanates and their utility in the synthesis of heterocycles, see
    • For a review on organic isothiocyanates and their utility in the synthesis of heterocycles, see : Mukerjee, A. K.; Ashare, R. Chem. Rev. 1991, 91, 1-24 and references cited therein.
    • (1991) Chem. Rev , vol.91 , pp. 1-24
    • Mukerjee, A.K.1    Ashare, R.2
  • 64
    • 68049099718 scopus 로고    scopus 로고
    • Dogadkin, B. A.; Pavlov, N. N. Dokl. Akad Nauk. SSSR 1961, 138, 1111. Chem. Abstr. 1961, 55, 24613a.
    • Dogadkin, B. A.; Pavlov, N. N. Dokl. Akad Nauk. SSSR 1961, 138, 1111. Chem. Abstr. 1961, 55, 24613a.
  • 72
    • 0000327516 scopus 로고
    • For coupling of amines with isothiocyanates, see: a
    • For coupling of amines with isothiocyanates, see: (a) Neville, R. G.; Mcgee, J. J. Can. J. Chem. 1963, 41, 2123-2129.
    • (1963) Can. J. Chem , vol.41 , pp. 2123-2129
    • Neville, R.G.1    Mcgee, J.J.2
  • 78
    • 0022960062 scopus 로고
    • For selected examples of glycosyl isothiocyanates applications, see: a
    • For selected examples of glycosyl isothiocyanates applications, see: (a) Witczak, Z. J. Adv. Carbohydr. Chem. Biochem. 1986, 44, 91-145.
    • (1986) Adv. Carbohydr. Chem. Biochem , vol.44 , pp. 91-145
    • Witczak, Z.J.1
  • 85
    • 68049105719 scopus 로고    scopus 로고
    • For the utility of sugar isothiocyanates in the synthesis of (i) N-nucleosides and glycosylaminoheterocycles, see: (a) Reference 31.
    • For the utility of sugar isothiocyanates in the synthesis of (i) N-nucleosides and glycosylaminoheterocycles, see: (a) Reference 31.
  • 88
    • 68049111965 scopus 로고    scopus 로고
    • N-Glycopeptides: (d) Seitz, O. ChemBioChem 2000, 1, 215-246.
    • (ii) N-Glycopeptides: (d) Seitz, O. ChemBioChem 2000, 1, 215-246.
  • 90
    • 0032541645 scopus 로고    scopus 로고
    • (f) Taylor, C. M. Tetrahedron 1998, 54, 11317-11362.
    • (1998) Tetrahedron , vol.54 , pp. 11317-11362
    • Taylor, C.M.1
  • 91
    • 33847026373 scopus 로고    scopus 로고
    • Glycoconjugates: (g) Rodriguez-Lucena, D.; Benito, J.; Ortiz Mellet, C.; Garcia Fernandez, J. M. Chem. Commun. 2007, 831-833.
    • (iii) Glycoconjugates: (g) Rodriguez-Lucena, D.; Benito, J.; Ortiz Mellet, C.; Garcia Fernandez, J. M. Chem. Commun. 2007, 831-833.
  • 95
    • 0029911174 scopus 로고    scopus 로고
    • Thioureabridged cluster glycosides from glycosyl isothiocyanates: (k) Lindhorst, T. K.; Kieburg, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1953-1956.
    • (iv) Thioureabridged cluster glycosides from glycosyl isothiocyanates: (k) Lindhorst, T. K.; Kieburg, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1953-1956.
  • 96
    • 68049095560 scopus 로고    scopus 로고
    • Linear and dendritic thiourea-linked glycooligomers: (l) Jiminez, Blanco, J. L.; Bootello, P.; Ortiz Mellet, C.; Garcia Fernandez, J. M. Eur. J. Org. Chem. 2006, 183-196.
    • (v) Linear and dendritic thiourea-linked glycooligomers: (l) Jiminez, Blanco, J. L.; Bootello, P.; Ortiz Mellet, C.; Garcia Fernandez, J. M. Eur. J. Org. Chem. 2006, 183-196.
  • 97
    • 15944376959 scopus 로고    scopus 로고
    • Antiviral, antibacterial and antitumour agents prepared by using glucosyl isothiocyanates and biologically active amines: (m) Garcia Fernandez, J. M.; Ortiz Mellet, C. Adv. Carbohydr. Chem. Biochem. 2000, 55, 35-135.
    • (vi) Antiviral, antibacterial and antitumour agents prepared by using glucosyl isothiocyanates and biologically active amines: (m) Garcia Fernandez, J. M.; Ortiz Mellet, C. Adv. Carbohydr. Chem. Biochem. 2000, 55, 35-135.
  • 99
    • 34748885101 scopus 로고    scopus 로고
    • Glycolipids for oral drug delivery: (o) Falconer, R. A.; Toth, I. Bioorg. Med. Chem. 2007, 15, 7012-7020.
    • (vii) Glycolipids for oral drug delivery: (o) Falconer, R. A.; Toth, I. Bioorg. Med. Chem. 2007, 15, 7012-7020.
  • 100
    • 0037239881 scopus 로고    scopus 로고
    • and references cited therein
    • Jagodzinski, T. S. Chem. Rev. 2003, 103, 197-227 and references cited therein.
    • (2003) Chem. Rev , vol.103 , pp. 197-227
    • Jagodzinski, T.S.1
  • 108
    • 0141789882 scopus 로고    scopus 로고
    • For the synthesis, isolation, and characterization studies of isocyanates derived from Fmoc-R-amino acids/peptide acids, see: (a) Patil, B. S.; Vasanthakumar, G. R.; Suresh Babu, V. V. J. Org. Chem. 2003, 68, 7274-7280.
    • For the synthesis, isolation, and characterization studies of isocyanates derived from Fmoc-R-amino acids/peptide acids, see: (a) Patil, B. S.; Vasanthakumar, G. R.; Suresh Babu, V. V. J. Org. Chem. 2003, 68, 7274-7280.
  • 111
    • 0000071911 scopus 로고    scopus 로고
    • A single example of the isothiocyanate, [[(1,1-dimethylethoxy)carbonyl] amino]ethylisothiocyanate, was prepared from ethylene diamine by treating mono Boc-protected ethylene diamine with carbon disulfide and DCC. The product was isolated after column purification in 92% yield: For details see: Kneeland, D. M.; Ariga, K.; Lynch, V. M.; Huang, C.-Y.; Anslyn, E. V. J. Am. Chem. Soc. 1993, 115, 10042-10055.
    • A single example of the isothiocyanate, [[(1,1-dimethylethoxy)carbonyl] amino]ethylisothiocyanate, was prepared from ethylene diamine by treating mono Boc-protected ethylene diamine with carbon disulfide and DCC. The product was isolated after column purification in 92% yield: For details see: Kneeland, D. M.; Ariga, K.; Lynch, V. M.; Huang, C.-Y.; Anslyn, E. V. J. Am. Chem. Soc. 1993, 115, 10042-10055.
  • 114
    • 36849093924 scopus 로고    scopus 로고
    • For the synthesis of N-protected R-amino formamides from Fmoc/Z-protected amino acids, see: (a) Sudarshan, N. S.; Narendra, N.; Hemantha, H. P.; Sureshbabu, V. V. J. Org. Chem. 2007, 72, 9804-9807.
    • For the synthesis of N-protected R-amino formamides from Fmoc/Z-protected amino acids, see: (a) Sudarshan, N. S.; Narendra, N.; Hemantha, H. P.; Sureshbabu, V. V. J. Org. Chem. 2007, 72, 9804-9807.
  • 116
    • 58149302872 scopus 로고    scopus 로고
    • For the synthesis of N-Fmoc-β-amino alkyl nitriles and their application in the preparation of 1-substituted tetrazoles, see: Sureshbabu, V. V.; Narendra, N.; Nagendra, G. J. Org. Chem. 2009, 74, 153-157.
    • For the synthesis of N-Fmoc-β-amino alkyl nitriles and their application in the preparation of 1-substituted tetrazoles, see: Sureshbabu, V. V.; Narendra, N.; Nagendra, G. J. Org. Chem. 2009, 74, 153-157.
  • 130
    • 0030426207 scopus 로고    scopus 로고
    • and references cited therein. For a review on X-ray diffraction analysis of N-protected amino acid halides, esters, anhydrides, UNCAs, azides, and amides see
    • For a review on X-ray diffraction analysis of N-protected amino acid halides, esters, anhydrides, UNCAs, azides, and amides see : Toniolo, C.; Crisma, M.; Formaggio, F. Biopolymers Peptide Science 1996, 40, 627-651 and references cited therein.
    • (1996) Biopolymers Peptide Science , vol.40 , pp. 627-651
    • Toniolo, C.1    Crisma, M.2    Formaggio, F.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.