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Volumn 80, Issue 1, 2012, Pages 17-26

Syntheses of Chiral N-(Protected) Tri- and Tetrapeptide Conjugates

Author keywords

Chemical structure; Heterocycles; Peptide; Steroids; Terpenes

Indexed keywords

STEROID; SUGAR; TERPENE; TETRAPEPTIDE; TETRAPEPTIDOYLBENZOTRIAZOLE; TRIPEPTIDE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 84862150173     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2012.01364.x     Document Type: Article
Times cited : (15)

References (35)
  • 1
    • 0032600640 scopus 로고    scopus 로고
    • A knowledge-based approach in designing combinatorial or medicinal chemistry libraries for drug discovery. 1. a qualitative and quantitative characterization of known drug databases
    • Ghose A.K., Viswanadhan V.N., Wendoloski J.J. (1999) A knowledge-based approach in designing combinatorial or medicinal chemistry libraries for drug discovery. 1. a qualitative and quantitative characterization of known drug databases. J Comb Chem;1:55-68.
    • (1999) J Comb Chem , vol.1 , pp. 55-68
    • Ghose, A.K.1    Viswanadhan, V.N.2    Wendoloski, J.J.3
  • 2
    • 84874499889 scopus 로고    scopus 로고
    • Biologically active peptides and enzymatic approaches to their production
    • Gill I., Lopez-Fandino R., Jorba X., Vulfson E.N. (1996) Biologically active peptides and enzymatic approaches to their production. Enzyme Microb Technol;18:162-183.
    • (1996) Enzyme Microb Technol , vol.18 , pp. 162-183
    • Gill, I.1    Lopez-Fandino, R.2    Jorba, X.3    Vulfson, E.N.4
  • 3
    • 1342302805 scopus 로고    scopus 로고
    • Recent development of peptide coupling reagents in organic synthesis
    • Han S.-Y., Kim Y.-A. (2004) Recent development of peptide coupling reagents in organic synthesis. Tetrahedron;60:2447-2467.
    • (2004) Tetrahedron , vol.60 , pp. 2447-2467
    • Han, S.-Y.1    Kim, Y.-A.2
  • 4
    • 26844576835 scopus 로고    scopus 로고
    • Amide bond formation and peptide coupling
    • Montalbetti C.A.G.N., Falque V. (2005) Amide bond formation and peptide coupling. Tetrahedron;61:10827-10852.
    • (2005) Tetrahedron , vol.61 , pp. 10827-10852
    • Montalbetti, C.A.G.N.1    Falque, V.2
  • 5
    • 4143095905 scopus 로고    scopus 로고
    • Ethyl propiolate: a simple and convenient peptide coupling reagent
    • Iorga B., Campagne J.-M. (2004) Ethyl propiolate: a simple and convenient peptide coupling reagent. Synlett;10:1826-1828.
    • (2004) Synlett , vol.10 , pp. 1826-1828
    • Iorga, B.1    Campagne, J.-M.2
  • 7
    • 84862126755 scopus 로고
    • Process for preparation of pure isomeric forms of 3,3,5-trimethylcyclohexanone and 3,3,5-trimethylcyclohexyl amino acid esters
    • FR Patent 19912654338, 1991
    • Laruelle C., Lepant M. (1992) Process for preparation of pure isomeric forms of 3, 3, 5-trimethylcyclohexanone and 3, 3, 5-trimethylcyclohexyl amino acid esters. FR Patent 19912654338, 1991; Chem Abstr;116:67183.
    • (1992) Chem Abstr , vol.116 , pp. 67183
    • Laruelle, C.1    Lepant, M.2
  • 8
    • 0000623282 scopus 로고
    • A simple method for the synthesis of long-chain alkyl esters of amino acids
    • Penney C.L., Shah P., Landi S. (1985) A simple method for the synthesis of long-chain alkyl esters of amino acids. J Org Chem;50:1457-1459.
    • (1985) J Org Chem , vol.50 , pp. 1457-1459
    • Penney, C.L.1    Shah, P.2    Landi, S.3
  • 9
    • 0027318961 scopus 로고
    • Biological roles of oligosaccharides: all of the theories are correct
    • Varki A. (1993) Biological roles of oligosaccharides: all of the theories are correct. Glycobiology;3:97-130.
    • (1993) Glycobiology , vol.3 , pp. 97-130
    • Varki, A.1
  • 10
    • 0001094662 scopus 로고    scopus 로고
    • Glycobiology: toward understanding the function of sugars
    • Dwek R.A. (1996) Glycobiology: toward understanding the function of sugars. Chem Rev;96:683-720.
    • (1996) Chem Rev , vol.96 , pp. 683-720
    • Dwek, R.A.1
  • 11
    • 0000440325 scopus 로고
    • Glycobiology: an expanding research area in carbohydrate chemistry
    • Kobata A. (1993) Glycobiology: an expanding research area in carbohydrate chemistry. Acc Chem Res;26:319-324.
    • (1993) Acc Chem Res , vol.26 , pp. 319-324
    • Kobata, A.1
  • 12
    • 0032567305 scopus 로고    scopus 로고
    • Use of onium salt-based coupling reagents in peptide synthesis
    • Albericio F., Bofill J.M., El-Faham A., Kates S.A. (1998) Use of onium salt-based coupling reagents in peptide synthesis. J Org Chem;63:9678-9683.
    • (1998) J Org Chem , vol.63 , pp. 9678-9683
    • Albericio, F.1    Bofill, J.M.2    El-Faham, A.3    Kates, S.A.4
  • 13
    • 0033548689 scopus 로고    scopus 로고
    • Addition of HOAt dramatically improves the effectiveness of pentafluorophenyl-based coupling reagents
    • Klose J., El-Faham A., Henklein P., Carpino L.A., Bienert M. (1999) Addition of HOAt dramatically improves the effectiveness of pentafluorophenyl-based coupling reagents. Tetrahedron Lett;40:2045-2048.
    • (1999) Tetrahedron Lett , vol.40 , pp. 2045-2048
    • Klose, J.1    El-Faham, A.2    Henklein, P.3    Carpino, L.A.4    Bienert, M.5
  • 14
    • 0000589494 scopus 로고    scopus 로고
    • From α-amino acids to peptides: all you need for the journey
    • Carpino L.A., Beyermann M., Wenschuh H., Bienert M. (1996) From α-amino acids to peptides: all you need for the journey. Acc Chem Res;29:268-274.
    • (1996) Acc Chem Res , vol.29 , pp. 268-274
    • Carpino, L.A.1    Beyermann, M.2    Wenschuh, H.3    Bienert, M.4
  • 15
    • 0025671995 scopus 로고
    • (9-Fluorenylmethyl)oxy]carbonyl (FMOC) amino acid fluorides. Convenient new peptide coupling reagents applicable to the FMOC/tert-butyl strategy for solution and solid-phase syntheses
    • Carpino L.A., Sadat-Aalaee D., Chao H.G., Desselms R.H. (1990) (9-Fluorenylmethyl)oxy]carbonyl (FMOC) amino acid fluorides. Convenient new peptide coupling reagents applicable to the FMOC/tert-butyl strategy for solution and solid-phase syntheses. J Am Chem Soc;112:9651-9652.
    • (1990) J Am Chem Soc , vol.112 , pp. 9651-9652
    • Carpino, L.A.1    Sadat-Aalaee, D.2    Chao, H.G.3    Desselms, R.H.4
  • 17
    • 0000791684 scopus 로고
    • 1,1′-Carbonylbis(3-methylimidazolium) triflate: an efficient reagent for aminoacylations
    • Saha A.K., Schultz P., Rapoport H. (1989) 1, 1′-Carbonylbis(3-methylimidazolium) triflate: an efficient reagent for aminoacylations. J Am Chem Soc;111:4856-4859.
    • (1989) J Am Chem Soc , vol.111 , pp. 4856-4859
    • Saha, A.K.1    Schultz, P.2    Rapoport, H.3
  • 19
    • 0033742916 scopus 로고    scopus 로고
    • Direct polycondensation of carboxylic acids and amines catalyzed by 3,4,5-trifluorophenylboronic acid
    • Ishihara K., Ohara S., Yamamoto H. (2000) Direct polycondensation of carboxylic acids and amines catalyzed by 3, 4, 5-trifluorophenylboronic acid. Macromolecules;33:3511-3513.
    • (2000) Macromolecules , vol.33 , pp. 3511-3513
    • Ishihara, K.1    Ohara, S.2    Yamamoto, H.3
  • 20
    • 77949835296 scopus 로고    scopus 로고
    • Solid-phase synthesis of peptide-viologen conjugates
    • Reczek J.J., Rebolini E., Urbach A.R. (2010) Solid-phase synthesis of peptide-viologen conjugates. J Org Chem;75:2111-2114.
    • (2010) J Org Chem , vol.75 , pp. 2111-2114
    • Reczek, J.J.1    Rebolini, E.2    Urbach, A.R.3
  • 21
    • 0037020736 scopus 로고    scopus 로고
    • An efficient and practical method for solid-phase synthesis of tripeptide-bearing glycopeptide antibiotics: combinatorial parallel synthesis of carboxamide derivatives of chloroorienticin B
    • Yasukata T., Shindo H., Yoshida O., Sumino Y., Munekage T., Narukawa Y., Nishitiani Y. (2002) An efficient and practical method for solid-phase synthesis of tripeptide-bearing glycopeptide antibiotics: combinatorial parallel synthesis of carboxamide derivatives of chloroorienticin B. Bioorg Med Chem Lett;12:3033-3036.
    • (2002) Bioorg Med Chem Lett , vol.12 , pp. 3033-3036
    • Yasukata, T.1    Shindo, H.2    Yoshida, O.3    Sumino, Y.4    Munekage, T.5    Narukawa, Y.6    Nishitiani, Y.7
  • 22
    • 1642575089 scopus 로고    scopus 로고
    • Synthesis of oligonucleotide 2′-conjugates via amide bond formation in solution
    • Kachalova A.V., Stetsenko D.A., Gait M.J., Oretskaya T.S. (2004) Synthesis of oligonucleotide 2′-conjugates via amide bond formation in solution. Bioorg Med Chem Lett;14:801-804.
    • (2004) Bioorg Med Chem Lett , vol.14 , pp. 801-804
    • Kachalova, A.V.1    Stetsenko, D.A.2    Gait, M.J.3    Oretskaya, T.S.4
  • 23
    • 0035051706 scopus 로고    scopus 로고
    • Novel ester-linked carbohydrate-peptide adducts: effect of the peptide substituent on the pathways of intramolecular reactions
    • Jeric I., Horvat S. (2001) Novel ester-linked carbohydrate-peptide adducts: effect of the peptide substituent on the pathways of intramolecular reactions. Eur J Org Chem; 1533-1539.
    • (2001) Eur J Org Chem , pp. 1533-1539
    • Jeric, I.1    Horvat, S.2
  • 24
    • 68149087433 scopus 로고    scopus 로고
    • Estrano[17,16-e]pyrimidine-amino acid and estrano[17,16-e]pyrimidine-peptide conjugates
    • Matsumoto T., Shiine K., Mataka S., Thiemann T. (2009) Estrano[17, 16-e]pyrimidine-amino acid and estrano[17, 16-e]pyrimidine-peptide conjugates. J Chem Res;39:1-396.
    • (2009) J Chem Res , vol.39 , pp. 1-396
    • Matsumoto, T.1    Shiine, K.2    Mataka, S.3    Thiemann, T.4
  • 25
    • 0442294196 scopus 로고    scopus 로고
    • A route to new galactosyl peptides: application to the synthesis of a galactosyl pentapeptide analogue of Leu-enkephalin
    • Coutrot F., Grison C., Coutrot P. (2004) A route to new galactosyl peptides: application to the synthesis of a galactosyl pentapeptide analogue of Leu-enkephalin. C R Chim;7:3-13.
    • (2004) C R Chim , vol.7 , pp. 3-13
    • Coutrot, F.1    Grison, C.2    Coutrot, P.3
  • 26
    • 0034549338 scopus 로고    scopus 로고
    • N-Acylbenzotriazoles: neutral acylating reagents for the preparation of primary, secondary, and tertiary amides
    • Katritzky A.R., He H.-Y., Suzuki K. (2000) N-Acylbenzotriazoles: neutral acylating reagents for the preparation of primary, secondary, and tertiary amides. J Org Chem;65:8210-8213.
    • (2000) J Org Chem , vol.65 , pp. 8210-8213
    • Katritzky, A.R.1    He, H.-Y.2    Suzuki, K.3
  • 27
    • 3242766001 scopus 로고    scopus 로고
    • One-pot synthesis of cinnamoyl hydrazides
    • Katritzky A.R., Wang M., Zhang S. (2001) One-pot synthesis of cinnamoyl hydrazides. Arkivoc;ix:19-23.
    • (2001) Arkivoc , vol.40 , pp. 19-23
    • Katritzky, A.R.1    Wang, M.2    Zhang, S.3
  • 28
    • 0038616398 scopus 로고    scopus 로고
    • Expedient acylations of primary and secondary alkyl cyanides to α-substituted β-ketonitriles
    • Katritzky A.R., Abdel-Fattah A.A.A., Wang M. (2003) Expedient acylations of primary and secondary alkyl cyanides to α-substituted β-ketonitriles. J Org Chem;68:4932-4934.
    • (2003) J Org Chem , vol.68 , pp. 4932-4934
    • Katritzky, A.R.1    Abdel-Fattah, A.A.A.2    Wang, M.3
  • 29
    • 0038676242 scopus 로고    scopus 로고
    • Regiospecific c-acylation of pyrroles and indoles using N-acylbenzotriazoles
    • Katritzky A.R., Suzuki K., Singh S.K., He H.-Y. (2003) Regiospecific c-acylation of pyrroles and indoles using N-acylbenzotriazoles. J Org Chem;68:5720-5723.
    • (2003) J Org Chem , vol.68 , pp. 5720-5723
    • Katritzky, A.R.1    Suzuki, K.2    Singh, S.K.3    He, H.-Y.4
  • 30
    • 67650021159 scopus 로고    scopus 로고
    • Efficient synthesis of azo dye labeled terpenes, sugars, and steroids using N-(4-arylazobenzoyl)-1H-benzotriazoles
    • Katritzky A.R., Tala S.R., Abo-Dya N.E., Abdel-Samii Z.K. (2009) Efficient synthesis of azo dye labeled terpenes, sugars, and steroids using N-(4-arylazobenzoyl)-1H-benzotriazoles. Synthesis;10:1708-1714.
    • (2009) Synthesis , vol.10 , pp. 1708-1714
    • Katritzky, A.R.1    Tala, S.R.2    Abo-Dya, N.E.3    Abdel-Samii, Z.K.4
  • 32
    • 70349295869 scopus 로고    scopus 로고
    • Chiral acylation with N-(protected α-aminoacyl)benzotriazoles for advantageous syntheses of peptides and peptide conjugates
    • Katritzky A.R., Angrish P., Todadze E. (2009) Chiral acylation with N-(protected α-aminoacyl)benzotriazoles for advantageous syntheses of peptides and peptide conjugates. Synlett;15:2392-2411.
    • (2009) Synlett , vol.15 , pp. 2392-2411
    • Katritzky, A.R.1    Angrish, P.2    Todadze, E.3
  • 33
    • 80052686684 scopus 로고    scopus 로고
    • Tri-, tetra- and pentapeptidoylbenzotriazoles: Novel synthetic intermediates
    • Abdelmajeid A., Tala S.R., Amine M.S., Katritzky A.R. (2011) Tri-, tetra- and pentapeptidoylbenzotriazoles: Novel synthetic intermediates. Synthesis;18:2995-3005.
    • (2011) Synthesis , vol.18 , pp. 2995-3005
    • Abdelmajeid, A.1    Tala, S.R.2    Amine, M.S.3    Katritzky, A.R.4
  • 34
    • 33846018414 scopus 로고    scopus 로고
    • Convenient and efficient preparation of N-protected (α-aminoacyl)oxy-substituted terpenes and alkanes
    • Katritzky A.R., Angrish P. (2006) Convenient and efficient preparation of N-protected (α-aminoacyl)oxy-substituted terpenes and alkanes. Synthesis;24:4135-4142.
    • (2006) Synthesis , vol.24 , pp. 4135-4142
    • Katritzky, A.R.1    Angrish, P.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.