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Volumn 19, Issue 11, 2012, Pages 1231-1236

Aqueous microwave-assisted solid-phase peptide synthesis using fmoc strategy: In-water synthesis of "difficult sequences"

Author keywords

Difficult sequence; Fmoc amino acid; Microwave assisted synthesis; Nanoparticles; Solid phase synthesis; Synthesis in water

Indexed keywords

ACYL CARRIER PEPTIDE; AMINO ACID; DERMOPHINAMIDE; FMOC AMINO ACID; LEUCINE ENKEPHALINAMIDE; NANOPARTICLE; PEPTIDE; UNCLASSIFIED DRUG; WATER;

EID: 84868011124     PISSN: 09298665     EISSN: None     Source Type: Journal    
DOI: 10.2174/092986612803217114     Document Type: Article
Times cited : (14)

References (34)
  • 2
    • 57249102969 scopus 로고    scopus 로고
    • Twelve more green chemistry principles
    • Winterton, N. Twelve more green chemistry principles. Green Chem., 2001, 3, G73-G75.
    • (2001) Green Chem. , vol.3
    • Winterton, N.1
  • 3
    • 36348937198 scopus 로고    scopus 로고
    • The e Factor: Fifteen years on
    • Sheldon, R.A. The E Factor: fifteen years on. Green Chem., 2007, 9, 1273-1283.
    • (2007) Green Chem. , vol.9 , pp. 1273-1283
    • Sheldon, R.A.1
  • 5
    • 0035660887 scopus 로고    scopus 로고
    • A new water-soluble N-protecting group, 2-(phenyl(methyl)sulfonio) ethyloxycarbonyl tetrafluoroborate, and its application to solid phase peptide synthesis in water
    • DOI 10.1002/psc.361
    • Hojo, K.; Maeda, M.; Kawasaki, K. A new water-soluble Nprotecting group, 2-[phenyl(methyl)sulfonio]ethyloxycarbonyl tetrafluoroborate, and its application to solid phase peptide synthesis in water. J. Peptide Sci., 2001, 7, 615-618. (Pubitemid 34026632)
    • (2001) Journal of Peptide Science , vol.7 , Issue.12 , pp. 615-618
    • Hojo, K.1    Maeda, M.2    Kawasaki, K.3
  • 6
    • 0842332277 scopus 로고    scopus 로고
    • A water-soluble N-protecting group, 2-[phenyl(methyl)sulfonio] ethoxycarbonyl tetrafluoroborate, and its application to peptide synthesis
    • Hojo, K.; Maeda, M.; Kawasaki, K. A water-soluble N-protecting group, 2-[phenyl(methyl)sulfonio] ethoxycarbonyl tetrafluoroborate, and its application to peptide synthesis. Tetrahedron, 2004, 60, 1875-1866.
    • (2004) Tetrahedron , vol.60 , pp. 1875-1866
    • Hojo, K.1    Maeda, M.2    Kawasaki, K.3
  • 7
    • 8544246407 scopus 로고    scopus 로고
    • 2-(4-Sulfophenylsulfonyl)ethoxycarbonyl group: A new water-soluble N-protecting group and its application to solid phase peptide synthesis in water
    • DOI 10.1016/j.tetlet.2004.10.095, PII S0040403904023263
    • Hojo, K.; Maeda, M.; Kawasaki, K. Tetrahedron Lett. 2-(4-Sulfophenyl) ethoxycarbonyl group: a new water-soluble Nprotecting group and its application to solid-phase peptide synthesis in water. Tetrahedron Lett., 2004, 45, 9293-9295. (Pubitemid 39491169)
    • (2004) Tetrahedron Letters , vol.45 , Issue.50 , pp. 9293-9295
    • Hojo, K.1    Maeda, M.2    Kawasaki, K.3
  • 8
    • 34447563915 scopus 로고    scopus 로고
    • Solid-phase peptide synthesis using nanoparticulate amino acids in water
    • DOI 10.1002/psc.874
    • Hojo, K.; Ichikawa, H.; Maeda, M.; Kida, S.; Fukumori, Y.; Kawasaki, K. Solid-phase peptide synthesis using nanoparticulate amino acids in water. J. Peptide Sci., 2007, 13, 493-497. (Pubitemid 47082901)
    • (2007) Journal of Peptide Science , vol.13 , Issue.7 , pp. 493-497
    • Hojo, K.1    Ichikawa, H.2    Maeda, M.3    Kida, S.4    Fukumori, Y.5    Kawasaki, K.6
  • 10
    • 80052025287 scopus 로고    scopus 로고
    • Development of a method for environmentally friendly chemical peptide synthesis in water using waterdispersible amino acid nanoparticles
    • Hojo, K.; Hara, A.; Kitai, H.; Onishi, M.; Ichikawa, H.; Fukumori, Y.; Kawasaki, K. Development of a method for environmentally friendly chemical peptide synthesis in water using waterdispersible amino acid nanoparticles. Chem. Central J., 2011, 5, 49.
    • (2011) Chem. Central J. , vol.5 , pp. 49
    • Hojo, K.1    Hara, A.2    Kitai, H.3    Onishi, M.4    Ichikawa, H.5    Fukumori, Y.6    Kawasaki, K.7
  • 12
    • 11144325118 scopus 로고    scopus 로고
    • Controlled microwave heating in modern organic synthesis
    • DOI 10.1002/anie.200400655
    • Kappe, C.O. Controlled microwave heating in modern organic synthesis. Angew. Chem. Int. Ed., 2004, 43, 6250-6284. (Pubitemid 40036603)
    • (2004) Angewandte Chemie - International Edition , vol.43 , Issue.46 , pp. 6250-6284
    • Kappe, C.O.1
  • 13
    • 0035813244 scopus 로고    scopus 로고
    • Microwave assisted organic synthesis - A review
    • DOI 10.1016/S0040-4020(01)00906-1, PII S0040402001009061
    • P. Lidström, J. Tierney, B. Wathey, J. Westman, Microwave assisted organic synthesis-a review. Tetrahedron, 2001, 57, 9225-9283. (Pubitemid 33016768)
    • (2001) Tetrahedron , vol.57 , Issue.45 , pp. 9225-9283
    • Lidstrom, P.1    Tierney, J.2    Wathey, B.3    Westman, J.4
  • 15
    • 0036360605 scopus 로고    scopus 로고
    • Rapid microwave-assisted solid phase peptide synthesis
    • Erdélyi, M.; Gogoll, A. Rapid microwave-assisted solid-phase peptide synthesis. Synthesis, 2002, 11, 1592-1596. (Pubitemid 34983389)
    • (2002) Synthesis , Issue.11 , pp. 1592-1596
    • Erdelyi, M.1    Gogoll, A.2
  • 16
    • 0000318227 scopus 로고
    • Enhanced coupling efficiency in solid-phase peptide synthesis by microwave irradiation
    • Yu, H.M.; Chen, S.T.; Wang, J.T. Enhanced coupling efficiency in solid-phase peptide synthesis by microwave irradiation. J. Org. Chem., 1992, 57, 4781-4784.
    • (1992) J. Org. Chem. , vol.57 , pp. 4781-4784
    • Yu, H.M.1    Chen, S.T.2    Wang, J.T.3
  • 17
    • 33750035585 scopus 로고    scopus 로고
    • Novel method for enhanced solid-phase peptide synthesis using microwave energy
    • Collins, J.M.; Collins, M.J. Novel method for enhanced solid-phase peptide synthesis using microwave energy. Biopolymers, 2003, 71, 361-366.
    • (2003) Biopolymers , vol.71 , pp. 361-366
    • Collins, J.M.1    Collins, M.J.2
  • 18
    • 47749088679 scopus 로고    scopus 로고
    • Aqueous microwave chemistry: A clean and green synthetic tool for rapid drug discovery
    • Polsehettiwar, V.; Varma, R.S. Aqueous microwave chemistry: a clean and green synthetic tool for rapid drug discovery. Chem. Soc. Rev., 2008, 37, 1546-1557.
    • (2008) Chem. Soc. Rev. , vol.37 , pp. 1546-1557
    • Polsehettiwar, V.1    Varma, R.S.2
  • 19
    • 33746288788 scopus 로고    scopus 로고
    • Microwave effects in organic synthesis: Mechanistic and reaction medium considerations
    • Loupy, A.; Varma, R.S. Microwave effects in organic synthesis: Mechanistic and reaction medium considerations. Chim. Oggi., 2006, 24, 36-40. (Pubitemid 44105477)
    • (2006) Chimica Oggi , vol.24 , Issue.3 , pp. 36-40
    • Loupy, A.1    Varma, R.S.2
  • 20
    • 70349920996 scopus 로고    scopus 로고
    • Solid-phase peptide synthesis in water using maicrowave assisted heating
    • Galanis, A.S.; Albericio, F.; Grøtli, M. Solid-phase peptide synthesis in water using maicrowave assisted heating. Org. Lett., 2009, 20, 4488-4491.
    • (2009) Org. Lett. , vol.20 , pp. 4488-4491
    • Galanis, A.S.1    Albericio, F.2    Grøtli, M.3
  • 21
    • 4544383493 scopus 로고    scopus 로고
    • Nanosuspensions in drug delivery
    • Rabinow, B.E. Nanosuspensions in drug delivery. Nat. Rev. Discov., 2004, 3, 785-795.
    • (2004) Nat. Rev. Discov. , vol.3 , pp. 785-795
    • Rabinow, B.E.1
  • 22
    • 33947463859 scopus 로고
    • The use of water-soluble and basic carbodiimides in peptide synthesis
    • Sheehan, J.C.; Hlavka, J.J. The use of water-soluble and basic carbodiimides in peptide synthesis. J. Org. Chem., 1956, 21, 439-441.
    • (1956) J. Org. Chem. , vol.21 , pp. 439-441
    • Sheehan, J.C.1    Hlavka, J.J.2
  • 23
    • 0344083921 scopus 로고    scopus 로고
    • Study on the activation of carboxylic acids by means of 2-chloro-4, 6-dimethoxy-1,3,5-triazine and 2-chloro-4,6-diphenoxy-1.3.5-triazine
    • Kaminski, Z.J.; Paneth, P.; Rudzinski, J. A. Study on the activation of carboxylic acids by means of 2-chloro-4,6-dimethoxy-1,3,5-triazine and 2-chloro-4,6-diphenoxy-1.3.5-triazine. J. Org. Chem., 1998, 63, 4248-4225.
    • (1998) J. Org. Chem. , vol.63 , pp. 4248-4225
    • Kaminski, Z.J.1    Paneth, P.2    Rudzinski, J.A.3
  • 24
    • 0033550301 scopus 로고    scopus 로고
    • 4-(4,6-Dimethoxy-1, 35-triazin-2-yl)-4-methyl-morpholinium chloride an efficient condensing agent leading to the formulation of amide and esters
    • Kunishima, M.; Kawachi, C.; Morita, J.; Terao, K.; Iawasaki, F.; Tani, S. 4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methyl-morpholinium chloride: an efficient condensing agent leading to the formulation of amide and esters. Tetrahedron, 1999, 55, 13159-13179.
    • (1999) Tetrahedron , vol.55 , pp. 13159-13179
    • Kunishima, M.1    Kawachi, C.2    Morita, J.3    Terao, K.4    Iawasaki, F.5    Tani, S.6
  • 25
    • 33947488929 scopus 로고
    • The use of esters of N-hydroxysuccinimide in peptide synthesis
    • Anderson, G.W.; Zimmerman, J.E.; Callahan, F.M. The use of esters of N-hydroxysuccinimide in peptide synthesis. J. Am. Chem. Soc., 1964, 86, 1839-1842.
    • (1964) J. Am. Chem. Soc. , vol.86 , pp. 1839-1842
    • Anderson, G.W.1    Zimmerman, J.E.2    Callahan, F.M.3
  • 26
    • 0001382352 scopus 로고
    • The effect of active ester components on recemization in the synthesis of peptides by the dicyclohexyl-carbodiimide method
    • Zimmerman, J.E.; Anderson, G.W. The effect of active ester components on recemization in the synthesis of peptides by the dicyclohexyl-carbodiimide method. J. Am. Chem. Soc., 1967, 89, 7151-7152.
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 7151-7152
    • Zimmerman, J.E.1    Anderson, G.W.2
  • 28
    • 0022512416 scopus 로고
    • Enhancement of N-hydroxysulfosuccinimide of water-soluble carbodiimide-mediated coupling reactions
    • Staros, J.V.; Wright, R.W.; Swingle, D.M. Enhancement by Nhydroxysulfosuccinimide of water-soluble carbodiimide-mediated coupling reactions. Anal. Biochem., 1986, 156, 220-222. (Pubitemid 16044423)
    • (1986) Analytical Biochemistry , vol.156 , Issue.1 , pp. 220-222
    • Staros, J.V.1    Wright, R.W.2    Swingle, D.M.3
  • 29
    • 17844395169 scopus 로고    scopus 로고
    • Application of microwave irradiation to the synthesis of 14-helical b-peptides
    • Murray, J.M.; Gellman, D.H. Application of microwave irradiation to the synthesis of 14-helical b-peptides. Org. Lett., 2005, 7, 1517-1520.
    • (2005) Org. Lett. , vol.7 , pp. 1517-1520
    • Murray, J.M.1    Gellman, D.H.2
  • 30
    • 54549091070 scopus 로고    scopus 로고
    • Advances in automatic, manual and microwave-assisted solid-phase peptide synthesis
    • Sabatino, G.; Papini, A.M. Advances in automatic, manual and microwave-assisted solid-phase peptide synthesis. Curr. Opin. Drug Discov. Dev., 2008, 11, 762-770.
    • (2008) Curr. Opin. Drug Discov. Dev. , vol.11 , pp. 762-770
    • Sabatino, G.1    Papini, A.M.2
  • 31
    • 53049110370 scopus 로고    scopus 로고
    • Solid-phase synthesis of difficult peptide sequences at elevated temperatures: A critical comparison of microwave and conventional heating technologies
    • Bacsa, B.; Horvati, K.; Bosze, S.; Andreae, F.; Kappe, C.O. Solid-Phase Synthesis of Difficult Peptide Sequences at Elevated Temperatures: A Critical Comparison of Microwave and Conventional Heating Technologies. J. Org. Chem., 2008, 73, 7532-7542.
    • (2008) J. Org. Chem. , vol.73 , pp. 7532-7542
    • Bacsa, B.1    Horvati, K.2    Bosze, S.3    Andreae, F.4    Kappe, C.O.5
  • 32
    • 62649143644 scopus 로고    scopus 로고
    • Microwave-matter effects in metal (oxide)-mediated chemistry and in drying
    • Caddick, S.; Fitzmaurice, R. Microwave-matter effects in metal (oxide)-mediated chemistry and in drying. Tetrahedron, 2009, 65, 3325-3355.
    • (2009) Tetrahedron , vol.65 , pp. 3325-3355
    • Caddick, S.1    Fitzmaurice, R.2
  • 33
    • 0000748775 scopus 로고
    • Solvation of the polymer matrix: Source of truncated and deletion sequences in solid phase synthesis
    • Hancock, D.J.; Prescott, R.P.; Vagelos, P.R.; Marshall, G.R. Solvation of the polymer matrix: source of truncated and deletion sequences in solid phase synthesis. J. Org. Chem., 1973, 38, 774-781.
    • (1973) J. Org. Chem. , vol.38 , pp. 774-781
    • Hancock, D.J.1    Prescott, R.P.2    Vagelos, P.R.3    Marshall, G.R.4
  • 34
    • 84912662415 scopus 로고
    • The role of crosslinked resin support in enhancing the solvation and reactivity of self-aggregating peptides solid-phase synthesis of acyl carrier protein (65-74)
    • Brubkfeldt, K., Ed.; Scriptor: Copenhagen
    • Kent, S.B.H.; Merrifield, R.B. The role of crosslinked resin support in enhancing the solvation and reactivity of self-aggregating peptides solid-phase synthesis of acyl carrier protein (65-74). Peptides 1980, Proceedings of the 16th Eouropean Peptide Symposium; Brubkfeldt, K., Ed.; Scriptor: Copenhagen, 1981, pp. 328-333.
    • (1981) Peptides 1980, Proceedings of the 16th Eouropean Peptide Symposium , pp. 328-333
    • Kent, S.B.H.1    Merrifield, R.B.2


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