메뉴 건너뛰기




Volumn 66, Issue 34, 2010, Pages 6718-6724

Isoselenocyanates derived from Boc/Z-amino acids: Synthesis, isolation, characterization, and application to the efficient synthesis of unsymmetrical selenoureas and selenoureidopeptidomimetics

Author keywords

Isoselenocyanates; Peptidomimetics; Selenoureas; Selenoureidopeptidomimetics

Indexed keywords

BENZYL 1 FORMAMIDO 4 (METHYLTHIO) BUTAN 2 YLCARBAMATE; BENZYL 1 ISOCYANO 3 PHENYLPROPAN 2 YLCARBAMATE; BENZYL 1 ISOSELENOCYANATOPROPAN 2 YLCARBAMATE; CARBAMIC ACID DERIVATIVE; ISOCYANATE; ISONITRILE DERIVATIVE; ISOSELENOCYANATE; ISOTHIOCYANIC ACID; METHYL 2 [3 [2 (BENZYLOXYCARBONYL) 4 (METHYLTHIO) BUTYL] SELENOUREIDO] PROPANOATE; PROPIONIC ACID DERIVATIVE; SELENIUM; SELENOUREA; SELENOUREIDOPEPTIDE; TERT BUTYL 1 [3 (3 CHLOROPHENYL) SELENOUREIDO] 3 METHYLBUTAN 2 YLCARBAMATE; TERT BUTYL 1 FORMAMIDO 3 METHYLBUTAN 2 YLCARBAMATE; TERT BUTYL 1 ISOCYANO 4 METHYLPENTAN 2 YLCARBAMATE; TERT BUTYL 1 ISOSELENOCYANATO 4 METHYLPENTAN 2 YLCARBAMATE; TRIETHYLAMINE; UNCLASSIFIED DRUG; UREA DERIVATIVE;

EID: 77955472297     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.06.082     Document Type: Article
Times cited : (25)

References (82)
  • 3
    • 27744455370 scopus 로고    scopus 로고
    • P.E. Nielsen, Wiley-VCH GmbH KGaA Weinheim, Germany
    • P.E. Nielsen, Pseudo-Peptides in Drug discovery 2004 Wiley-VCH GmbH KGaA Weinheim, Germany and references cited therein
    • (2004) Pseudo-Peptides in Drug Discovery
  • 6
    • 0003616384 scopus 로고
    • O.A. Levander, W. Mertz, Academic Orlando, FL
    • For biological role of OrgSeCs including nutritional significance of Se see: O.A. Levander, W. Mertz, Selenium in Trace Elements in Human and Animal Nutrition Vol. 2 1986 Academic Orlando, FL 209
    • (1986) Selenium in Trace Elements in Human and Animal Nutrition , vol.2 , pp. 209
  • 7
    • 0035385139 scopus 로고    scopus 로고
    • For the chemistry of biologically important synthetic OrgSeCs see: G. Mugesh, W.-W. du Mont, and H. Sies Chem. Rev. 101 2001 2125 2180
    • (2001) Chem. Rev. , vol.101 , pp. 2125-2180
    • Mugesh, G.1    Du Mont, W.-W.2    Sies, H.3
  • 27
    • 27144466069 scopus 로고    scopus 로고
    • (i) For (1→n) linked selenodisaccharides synthesis
    • (i) For (1→n) linked selenodisaccharides synthesis see: Y. Kawai, H. Ando, H. Ozeki, M. Koketsu, and H. Ishihara Org. Lett. 7 2005 4653 4656
    • (2005) Org. Lett. , vol.7 , pp. 4653-4656
    • Kawai, Y.1    Ando, H.2    Ozeki, H.3    Koketsu, M.4    Ishihara, H.5
  • 30
  • 37
    • 61849094302 scopus 로고    scopus 로고
    • For a recent review on selenopeptide chemistry including a summary of peptides and proteins synthesized such as selenoglutathione, selenooxytocin, somatostatin, selenosubtilisin, metalloselenoein, selenoglutathione, glutaredoxin, endothelin-1, apamin, interleukin, [C754U]-RNA (745-761), [C110U]-RNase A, [C38U]-BPTI, conotoxin ImI, glutaredoxin 3, see: M. Muttenthaler, and P.F. Alewood J. Pept. Sci. 14 2008 1223 1239 and references cited therein
    • (2008) J. Pept. Sci. , vol.14 , pp. 1223-1239
    • Muttenthaler, M.1    Alewood, P.F.2
  • 47
    • 77955466613 scopus 로고    scopus 로고
    • note
    • For reviews on incorporation of Sec through the biosynthetic routes including expressed protein ligation, transfection of eukaryotic cells, recombinant seleproduction techniques see:
  • 55
    • 0000279927 scopus 로고
    • (i) For the synthesis of aliphatic isoselenocyanates
    • (i) For the synthesis of aliphatic isoselenocyanates see: N. Sonoda, G. Yamamoto, and S. Tsutsumi Bull. Chem. Soc. Jpn. 45 1972 2937 2938
    • (1972) Bull. Chem. Soc. Jpn. , vol.45 , pp. 2937-2938
    • Sonoda, N.1    Yamamoto, G.2    Tsutsumi, S.3
  • 56
  • 67
    • 77955467626 scopus 로고    scopus 로고
    • note
    • For a protocol to isoselenocyanates preparation via cycloaddition by the reaction of nitrile oxides with selenoamides see: Ref. 34b.
  • 72
    • 46749102507 scopus 로고    scopus 로고
    • For the generation of isocyanates starting from Boc-amino acids and their conversion to O-succinimidyl carbamates: V.V. Sureshbabu, N.S. Sudarshan, and Kantharaju Synth. Commun. 38 2008 2168 2184
    • (2008) Synth. Commun. , vol.38 , pp. 2168-2184
    • Sureshbabu, V.V.1    Sudarshan, N.S.2    Kantharaju3
  • 74
    • 0033550306 scopus 로고    scopus 로고
    • For the generation of isocyanates derived from β-amino acids and their conversion to active carbamates using Boc-chemistry
    • For the generation of isocyanates derived from β-amino acids and their conversion to active carbamates using Boc-chemistry see: G. Guichard, V. Semetey, C. Didierjean, A. Aubry, J.-P. Briand, and M. Rodriguez J. Org. Chem. 64 1999 8702 8705
    • (1999) J. Org. Chem. , vol.64 , pp. 8702-8705
    • Guichard, G.1    Semetey, V.2    Didierjean, C.3    Aubry, A.4    Briand, J.-P.5    Rodriguez, M.6
  • 78
    • 77955471295 scopus 로고    scopus 로고
    • note
    • For useful discussion of formamide and isonitrile derivatives of N-protected amino acids, literature protocols for their preparation and their applications, see Supplementary data.
  • 81
    • 33750738055 scopus 로고    scopus 로고
    • For selected reports on selenoureas from 2001 onwards
    • For selected reports on selenoureas from 2001 onwards, see: M. Koketsu, and H. Ishihara Curr. Org. Synth. 3 2006 439 455
    • (2006) Curr. Org. Synth. , vol.3 , pp. 439-455
    • Koketsu, M.1    Ishihara, H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.