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Volumn 55, Issue 2, 2000, Pages 110-119

(1H-Benzotriazol-1-yloxy)-N,N-dimethylmethaniminium hexachloroantimonate (BOMI), a novel coupling reagent for solution and solid-phase peptide synthesis

Author keywords

BOMI; Coupling efficiency; HOBt ester; Racemization; Reactivity; Solid phase peptide synthesis

Indexed keywords

BASE; BENZOTRIAZOLE DERIVATIVE; LEUCINE ENKEPHALIN; OLIGOPEPTIDE; PHOSPHONIUM DERIVATIVE; REAGENT; SOLVENT;

EID: 0033970478     PISSN: 1397002X     EISSN: None     Source Type: Journal    
DOI: 10.1034/j.1399-3011.2000.00158.x     Document Type: Article
Times cited : (12)

References (17)
  • 1
    • 49549139072 scopus 로고
    • Reactifs de couplage peptidique IV (1) - L'hexa-fluorophosphate de benzotriazolyl N-oxytrisdimethyl-amino phosphonium
    • 1. Castro, B., Dromoy, J.R., Evin, G. & Selve, C. (1975) Reactifs de couplage peptidique IV (1) - L'hexa-fluorophosphate de benzotriazolyl N-oxytrisdimethyl-amino phosphonium. Tetrahedron Lett. 16, 1219-1222.
    • (1975) Tetrahedron Lett. , vol.16 , pp. 1219-1222
    • Castro, B.1    Dromoy, J.R.2    Evin, G.3    Selve, C.4
  • 2
    • 49349126081 scopus 로고
    • L'hexafluorophosphate de O-benzotriazolyl-N,N-trtra-methyluronium: Un reactif de couplage peptidique nouveau et efficace
    • 2. Dourtoglou, V., Ziegler, J.C. & Gross, B. (1978) L'Hexafluorophosphate de O-benzotriazolyl-N,N-trtra-methyluronium: un reactif de couplage peptidique nouveau et efficace. Tetrahedron Lett. 19, 1269-1272.
    • (1978) Tetrahedron Lett. , vol.19 , pp. 1269-1272
    • Dourtoglou, V.1    Ziegler, J.C.2    Gross, B.3
  • 3
    • 0021159751 scopus 로고
    • O-benzotriazolyl-N,N,N′,N′-tetramethyluronium hexafluorophosphate as coupling reagent for the synthesis of peptides of biological interest
    • 3. Dourtoglou, V. & Gross, B. (1984) O-Benzotriazolyl-N,N,N′,N′-tetramethyluronium hexafluorophosphate as coupling reagent for the synthesis of peptides of biological interest. Synthesis 572-574.
    • (1984) Synthesis , pp. 572-574
    • Dourtoglou, V.1    Gross, B.2
  • 4
    • 0025014627 scopus 로고
    • ℜ : A new peptide coupling reagent devoid of toxicby-product
    • ℜ : a new peptide coupling reagent devoid of toxicby-product. Tetrahedron Lett. 31, 205-208.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 205-208
    • Coste, J.1    Le-Nguyen, D.2    Castro, B.3
  • 5
    • 0026598905 scopus 로고
    • A new coupling reagent for peptide synthesis. Benzotriazoloxy-bis (pyrrolidino)-carbonium hexafluorophosphate (BBC)
    • 5. Chen, S.Q. & Xu, J.C. (1992) A new coupling reagent for peptide synthesis. Benzotriazoloxy-bis (pyrrolidino)-carbonium hexafluorophosphate (BBC). Tetrahedron Lett. 33, 647-650.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 647-650
    • Chen, S.Q.1    Xu, J.C.2
  • 6
    • 0025868658 scopus 로고
    • Oxybenzotriazole free peptide coupling reagents for N-methylated amino acids
    • 6. Coste, J., Frerot, E. & Jouin, P. (1991) Oxybenzotriazole free peptide coupling reagents for N-methylated amino acids. Tetrahedron Lett. 32, 1967-1970.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 1967-1970
    • Coste, J.1    Frerot, E.2    Jouin, P.3
  • 7
    • 0002870324 scopus 로고
    • New uronium salts as coupling reagents in peptide chemistry
    • (Giralt, E. & Andreu, D., eds). ESCOM Science, Leiden, The Netherlands
    • 7. Henklein, P., Beyermann, M., Bienert, M. & Knorr, R. (1991) New uronium salts as coupling reagents in peptide chemistry. In Proceedings of the Twenty-First European Peptide Symposium (Giralt, E. & Andreu, D., eds). ESCOM Science, Leiden, The Netherlands, pp. 67-68.
    • (1991) Proceedings of the Twenty-First European Peptide Symposium , pp. 67-68
    • Henklein, P.1    Beyermann, M.2    Bienert, M.3    Knorr, R.4
  • 8
    • 0026448849 scopus 로고
    • Efficient solid phase peptide synthesis. Use of methanesulfonic acid α-amino deprotecting procedure and new coupling reagent, 2-(benzotriazol-1-yl) oxy-1,3-dimethylimidazolidinium hexafluorophosphate (BOI)
    • 8. Kiso, Y., Fujiwara, Y., Kimura, T., Nishitani, A. & Akaji, K. (1992) Efficient solid phase peptide synthesis. Use of methanesulfonic acid α-amino deprotecting procedure and new coupling reagent, 2-(benzotriazol-1-yl) oxy-1,3-dimethylimidazolidinium hexafluorophosphate (BOI). Int. J. Peptide Protein Res. 40, 308-314.
    • (1992) Int. J. Peptide Protein Res. , vol.40 , pp. 308-314
    • Kiso, Y.1    Fujiwara, Y.2    Kimura, T.3    Nishitani, A.4    Akaji, K.5
  • 9
    • 0000749379 scopus 로고
    • Coupling N-methylated amino acids using PyBroP and PyCloP halogenophosphonium salts: Mechanism and field of application
    • 9. Coste, J., Frerot, E. & Jouin, P. (1994) Coupling N-methylated amino acids using PyBroP and PyCloP halogenophosphonium salts: mechanism and field of application. J. Org. Chem. 59, 2437-2446.
    • (1994) J. Org. Chem. , vol.59 , pp. 2437-2446
    • Coste, J.1    Frerot, E.2    Jouin, P.3
  • 10
    • 33845312505 scopus 로고
    • Advantageous applications of azabenzotriazole (triazolopyridine)-based coupling reagents to solid-phase peptide synthesis
    • 10. Carpino, L.A., El-Faham, A., Minor, C.A. & Albericio, F. (1994) Advantageous applications of azabenzotriazole (triazolopyridine)-based coupling reagents to solid-phase peptide synthesis. J. Chem. Soc. Chem. Commun. 201-203.
    • (1994) J. Chem. Soc. Chem. Commun. , pp. 201-203
    • Carpino, L.A.1    El-Faham, A.2    Minor, C.A.3    Albericio, F.4
  • 11
    • 0000898966 scopus 로고
    • Crystal structure of 3-(N-tritylmethionyl) benzotriazole 1-oxide, a synthon in peptide synthesis
    • 11. Barlos, K., Papaioannou, D. & Voliotis, S. (1985) Crystal structure of 3-(N-tritylmethionyl) benzotriazole 1-oxide, a synthon in peptide synthesis. J. Org. Chem. 50, 696-697.
    • (1985) J. Org. Chem. , vol.50 , pp. 696-697
    • Barlos, K.1    Papaioannou, D.2    Voliotis, S.3
  • 12
    • 0007193238 scopus 로고    scopus 로고
    • Chemical synthesis of natural product peptides: Coupling methods for incorporation of noncoded amino acids into peptides
    • 12. Humphrey, J.M. & Chamberlin, A.R. (1997) Chemical synthesis of natural product peptides: coupling methods for incorporation of noncoded amino acids into peptides. Chem. Rev. 97, 2243-2266.
    • (1997) Chem. Rev. , vol.97 , pp. 2243-2266
    • Humphrey, J.M.1    Chamberlin, A.R.2
  • 13
    • 12044258245 scopus 로고
    • 1-Hydroxy-7-azabenzotriazole. An efficient peptide coupling additive
    • 13. Carpino, L.A. (1993) 1-Hydroxy-7-azabenzotriazole. An efficient peptide coupling additive. J. Am. Chem. Soc. 115, 4397-4398.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 4397-4398
    • Carpino, L.A.1
  • 14
    • 0033617325 scopus 로고    scopus 로고
    • BOMI-A novel peptide coupling reagent
    • 14. Li, P. & Xu, J.C. (1999) BOMI - a novel peptide coupling reagent. Tetrahedron Lett. 40, 3605-3608.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 3605-3608
    • Li, P.1    Xu, J.C.2
  • 16
    • 55549083919 scopus 로고
    • Amino-acids and pcptides, part XVI. Further studies of raccmisation during peptidc synthesis
    • 16. Williams, M.W. & Young, G.T. (1963) Amino-acids and pcptides, part XVI. Further studies of raccmisation during peptidc synthesis. J. Chem. Soc. 881-889.
    • (1963) J. Chem. Soc. , pp. 881-889
    • Williams, M.W.1    Young, G.T.2
  • 17
    • 0025195302 scopus 로고
    • 14N NMR studies of Leu-enkephalin and enkephalin-related fragments in aqueous solution
    • 14N NMR studies of Leu-enkephalin and enkephalin-related fragments in aqueous solution. Biopolymers 29, 423-439.
    • (1990) Biopolymers , vol.29 , pp. 423-439
    • Karayannis, T.1    Gerothanassis, L.P.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.