메뉴 건너뛰기




Volumn 20, Issue 10, 2013, Pages 1122-1128

Aqueous microwave-assisted solid-phase peptide synthesis using Fmoc strategy. II. Racemization studies and water based synthesis of cysteine-containing peptides

Author keywords

Cysteine; Microwave assisted synthesis; Nanoparticles; Racemization solid phase peptide synthesis; Synthesis in water

Indexed keywords

9 FLUORENYLMETHYL CHLOROFORMATE; CYSTEINE; NANOPARTICLE; OXYTOCIN DERIVATIVE; WATER;

EID: 84887939160     PISSN: 09298665     EISSN: None     Source Type: Journal    
DOI: 10.2174/0929866511320100006     Document Type: Article
Times cited : (11)

References (30)
  • 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
  • 4
    • 0035660887 scopus 로고    scopus 로고
    • A new water-soluble Nprotecting group, 2-[phenyl(methyl)sulfonio] ethyloxycarbonyl tetrafluoroborate, and its application to solid phase peptide synthesis in water
    • 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.
    • (2001) J. Peptide Sci. , vol.7 , pp. 615-618
    • Hojo, K.1    Maeda, M.2    Kawasaki, K.3
  • 5
    • 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
  • 6
    • 8544246407 scopus 로고    scopus 로고
    • 2-(4-Sulfophenyl)ethoxycarbonyl group: A new water-soluble Nprotecting group and its application to solid-phase peptide synthesis in water
    • Hojo, K.; Maeda, M.; Kawasaki, K. 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.
    • (2004) Tetrahedron Lett. , vol.45 , pp. 9293-9295
    • Hojo, K.1    Maeda, M.2    Kawasaki, K.3
  • 7
  • 9
    • 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. Cent. J., 2011, 5, 49.
    • (2011) Chem. Cent. 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
  • 10
    • 84868011124 scopus 로고    scopus 로고
    • Aqueous microwave-assisted solid-phase peptide synthesis using Fmoc strategy: In-water synthesis of "difficult sequences"
    • Hojo, K; Ichikawa, H.; Hara, A.; Onishi, M.; Kawasaki, K.; Fukumori, Y. Aqueous microwave-assisted solid-phase peptide synthesis using Fmoc strategy: in-water synthesis of "difficult sequences". Protein Pept. Lett., 2012, 19, 1231-1236.
    • (2012) Protein Pept. Lett. , vol.19 , pp. 1231-1236
    • Hojo, K.1    Ichikawa, H.2    Hara, A.3    Onishi, M.4    Kawasaki, K.5    Fukumori, Y.6
  • 12
    • 11144325118 scopus 로고    scopus 로고
    • Controlled microwave heating in modern organic synthesis
    • Kappe, C.O. Controlled microwave heating in modern organic synthesis. Angew. Chem. Int. Ed., 2004, 43, 6250-6284.
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 6250-6284
    • Kappe, C.O.1
  • 13
  • 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.
    • (2002) Synthesis , vol.11 , pp. 1592-1596
    • Erdélyi, 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
    • 33947207869 scopus 로고    scopus 로고
    • Limiting racemization and aspartimide formation in microwave-enhanced Fmoc solid phase peptide synthesis
    • Palasek, S.A.; Cox, Z.J.; Collins, J.M. Limiting racemization and aspartimide formation in microwave-enhanced Fmoc solid phase peptide synthesis. J. Pept. Sci., 2007, 13, 143-148.
    • (2007) J. Pept. Sci. , vol.13 , pp. 143-148
    • Palasek, S.A.1    Cox, Z.J.2    Collins, J.M.3
  • 19
    • 73349124783 scopus 로고    scopus 로고
    • Microwave-assisted solid-phase peptide synthesis at 60°C: Alternative conditions with low enatiomerization
    • Loffrendo, C.; Assunção N.A.; Gerhardt, J.; Miranda M.T.M. Microwave-assisted solid-phase peptide synthesis at 60°C: alternative conditions with low enatiomerization. J. Pept. Sci., 2009, 15, 808-817.
    • (2009) J. Pept. Sci. , vol.15 , pp. 808-817
    • Loffrendo, C.1    Assunção, N.A.2    Gerhardt, J.3    Miranda, M.T.M.4
  • 20
    • 0000277428 scopus 로고    scopus 로고
    • Occurrence and minimization of cysteine racemization during stepwise solid-phase peptide synthesis
    • Han, Y.; Albericio, F.; Barany, G. Occurrence and minimization of cysteine racemization during stepwise solid-phase peptide synthesis. J. Org. Chem., 1997, 62, 4307-4312.
    • (1997) J. Org. Chem. , vol.62 , pp. 4307-4312
    • Han, Y.1    Albericio, F.2    Barany, G.3
  • 21
    • 0036830576 scopus 로고    scopus 로고
    • Practical protocols for stepwise solid-phase synthesis of cysteine-containing peptides
    • Angell, Y.M.; Alsina, J.; Albericio, F.; Barany, G. Practical protocols for stepwise solid-phase synthesis of cysteine-containing peptides. J. Pept. Res., 2002, 60, 292-299.
    • (2002) J. Pept. Res. , vol.60 , pp. 292-299
    • Angell, Y.M.1    Alsina, J.2    Albericio, F.3    Barany, G.4
  • 22
    • 37049121311 scopus 로고
    • Racemization in peptide chemistry. Mechanism-specific models
    • Bodanszky, M.; Bodanszky A. Racemization in peptide chemistry. Mechanism-specific models. Chem. Commun., 1967, 591-592.
    • (1967) Chem. Commun. , pp. 591-592
    • Bodanszky, M.1    Bodanszky, A.2
  • 24
    • 0030020427 scopus 로고    scopus 로고
    • Racemization studies of Fmoc-Cys(Trt)-OH during stepwise Fmoc-solid phase peptide synthesis
    • Kaiser, T.; Nicholson, G.; Kohlbau, H.; Voleter, R.; Racemization studies of Fmoc-Cys(Trt)-OH during stepwise Fmoc-solid phase peptide synthesis. Tetrahedron Lett., 1996, 37, 1187-1190.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 1187-1190
    • Kaiser, T.1    Nicholson, G.2    Kohlbau, H.3    Voleter, R.4
  • 25
    • 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
  • 26
    • 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
  • 27
    • 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
  • 28
    • 0033550301 scopus 로고    scopus 로고
    • 4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium 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-methylmorpholinium 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
  • 29
    • 0022512416 scopus 로고
    • Enhancement by nhydroxysulfosuccinimide 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.
    • (1986) Anal. Biochem. , vol.156 , pp. 220-222
    • Staros, J.V.1    Wright, R.W.2    Swingle, D.M.3
  • 30
    • 0014772602 scopus 로고
    • Color test for detection of free terminal amino groups in the solid phase synthesis of peptide
    • Kaiser, E.; Colescott, R.L.; Bossinger, C.D.; Cook, P.I. Color test for detection of free terminal amino groups in the solid phase synthesis of peptide. Anal. Biochem., 1970, 34, 595-598. Technology
    • (1970) Anal. Biochem. , vol.34 , pp. 595-598
    • Kaiser, E.1    Colescott, R.L.2    Bossinger, C.D.3    Cook, P.I.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.