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Volumn 18, Issue 1, 2013, Pages 1111-1121

Solid phase versus solution phase synthesis of heterocyclic macrocycles

Author keywords

Cytotoxic; Heterocycle; Macrocycle; Oxazole; Peptides; Solid phase peptide synthesis; Telomestatin; Thiazole; Urukthapelstatin A

Indexed keywords

CYCLOPEPTIDE; CYSTEINE; DRUG DERIVATIVE; LEUCINE; SERINE; THIAZOLE DERIVATIVE; URUKTHAPELSTATIN A;

EID: 84872854944     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules18011111     Document Type: Article
Times cited : (16)

References (54)
  • 1
    • 33746634345 scopus 로고    scopus 로고
    • Breakthroughs in manufacturing are making large-scale synthesis of peptides a viable proposition
    • Jarvis, L.M. Breakthroughs in manufacturing are making large-scale synthesis of peptides a viable proposition. C E News 2006, 84, 23-25.
    • (2006) C E News , vol.84 , pp. 23-25
    • Jarvis, L.M.1
  • 2
    • 57349171593 scopus 로고    scopus 로고
    • N-Methylation of peptides: A new perspective in medicinal chemistry
    • Chatterjee, J.; Gilon, C.; Hoffman, A.; Kessler, H. N-Methylation of peptides: A new perspective in medicinal chemistry. Acc. Chem. Res. 2008, 41, 1331-1342.
    • (2008) Acc. Chem. Res. , vol.41 , pp. 1331-1342
    • Chatterjee, J.1    Gilon, C.2    Hoffman, A.3    Kessler, H.4
  • 4
    • 62949096175 scopus 로고    scopus 로고
    • Modified low molecular weight cyclic peptides as mimetics of BDNF with improved potency, proteolytic stability and transmembrane
    • Fletcher, J.M.; Hughes, R.A. Modified low molecular weight cyclic peptides as mimetics of BDNF with improved potency, proteolytic stability and transmembrane. Bioorg. Med. Chem. 2009, 17, 2695-2702.
    • (2009) Bioorg. Med. Chem. , vol.17 , pp. 2695-2702
    • Fletcher, J.M.1    Hughes, R.A.2
  • 5
    • 78249233244 scopus 로고    scopus 로고
    • Antimicrobial peptides, the ancient arm of the human immune system
    • Wiesner, J.; Vilcinskas, A. Antimicrobial peptides, the ancient arm of the human immune system. Virulence 2010, 1, 440-464.
    • (2010) Virulence , vol.1 , pp. 440-464
    • Wiesner, J.1    Vilcinskas, A.2
  • 6
    • 0029084673 scopus 로고
    • Macrocyclic peptidomimetics-Forcing peptides into bioactive conformations
    • Fairlie, D.P.; Abbenante, G.; March, D.R. Macrocyclic peptidomimetics-Forcing peptides into bioactive conformations. Curr. Med. Chem. 1995, 2, 654-686.
    • (1995) Curr. Med. Chem. , vol.2 , pp. 654-686
    • Fairlie, D.P.1    Abbenante, G.2    March, D.R.3
  • 7
    • 14944383798 scopus 로고    scopus 로고
    • The evolving role of natural products in drug discovery
    • Koehn, F.E.; Carter, G.T. The evolving role of natural products in drug discovery. Nat. Rev. Drug Discov. 2005, 4, 206-220.
    • (2005) Nat. Rev. Drug Discov. , vol.4 , pp. 206-220
    • Koehn, F.E.1    Carter, G.T.2
  • 8
    • 0036158878 scopus 로고    scopus 로고
    • Peptides as Drugs: Is there a Market?
    • Loffet, A. Peptides as Drugs: Is there a Market? Eur. Pept. Soc. 2002, 8, 1-7.
    • (2002) Eur. Pept. Soc. , vol.8 , pp. 1-7
    • Loffet, A.1
  • 12
    • 36749071496 scopus 로고    scopus 로고
    • Aplidine: A paradigm of how to handle the activity and toxicity of a novel marine anticancer poison
    • Le Tourneau, C.; Raymond, E.; Faivre, S. Aplidine: A paradigm of how to handle the activity and toxicity of a novel marine anticancer poison. Curr. Pharm. Des. 2007, 13, 3427-3429.
    • (2007) Curr. Pharm. Des. , vol.13 , pp. 3427-3429
    • Le Tourneau, C.1    Raymond, E.2    Faivre, S.3
  • 13
    • 34547223063 scopus 로고    scopus 로고
    • Urukthapelstatin A a novel cytotoxic substance from marine-derived Mechercharimyces asporophorigenes YM11-542 II physcico-chemical properties and structural elucidation
    • Matsuo, Y.; Kanoh, K.; Imanaka, H.; Adachi, K.; Nishizawa, M.; Shizuri, Y. Urukthapelstatin A, a novel cytotoxic substance from marine-derived Mechercharimyces asporophorigenes YM11-542 II physcico-chemical properties and structural elucidation. J. Antibiot. 2007, 60, 256-260.
    • (2007) J. Antibiot. , vol.60 , pp. 256-260
    • Matsuo, Y.1    Kanoh, K.2    Imanaka, H.3    Adachi, K.4    Nishizawa, M.5    Shizuri, Y.6
  • 14
    • 34547184566 scopus 로고    scopus 로고
    • Urukthapelstatin A a novel cytotoxic substance from marine-derived Mechercharimyces asporophorigenes YM11-542 I fermentation, isolation, and biological properties
    • Matsuo, Y.; Kanoh, K.; Yamori, T.; Kasai, H.; Katsuta, A.; Adachi, K.; Shin-ya, K.; Shizuri, Y. Urukthapelstatin A, a novel cytotoxic substance from marine-derived Mechercharimyces asporophorigenes YM11-542 I fermentation, isolation, and biological properties. J. Antibiot. 2007, 60, 251-255.
    • (2007) J. Antibiot. , vol.60 , pp. 251-255
    • Matsuo, Y.1    Kanoh, K.2    Yamori, T.3    Kasai, H.4    Katsuta, A.5    Adachi, K.6    Shin-ya, K.7    Shizuri, Y.8
  • 15
    • 44249111019 scopus 로고    scopus 로고
    • The thuggacins, novel antibacterial macrolides from sorangium cellulosum acting against selected gram-positive bacteria
    • Irschik, H.; Reichenbach, H.; Hofle, G.; Jansen, R. The thuggacins, novel antibacterial macrolides from sorangium cellulosum acting against selected gram-positive bacteria. J. Antibiot. 2007, 60, 733-738.
    • (2007) J. Antibiot. , vol.60 , pp. 733-738
    • Irschik, H.1    Reichenbach, H.2    Hofle, G.3    Jansen, R.4
  • 16
    • 23744461968 scopus 로고    scopus 로고
    • Directly linked polyazoles: Important moieties in natural products
    • Riego, E.; Hernández, D.; Albericio, F.; Álvarez, M. Directly linked polyazoles: Important moieties in natural products. Synthesis 2005, 2005, 1907-1922.
    • (2005) Synthesis , vol.2005 , pp. 1907-1922
    • Riego, E.1    Hernández, D.2    Albericio, F.3    Álvarez, M.4
  • 17
    • 46049100010 scopus 로고    scopus 로고
    • Total synthesis and molecular target of Largazole, a histone deacetylase inhibitor
    • Ying, Y.; Taori, K.; Kim, H.; Hong, J.; Luesch, H. Total synthesis and molecular target of Largazole, a histone deacetylase inhibitor. J. Am. Chem. Soc. 2008, 130, 8455-8459.
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 8455-8459
    • Ying, Y.1    Taori, K.2    Kim, H.3    Hong, J.4    Luesch, H.5
  • 19
    • 19644386054 scopus 로고    scopus 로고
    • Mechercharmycins A and B, cytotoxic substances from marine-derived thermoactinomyces sp. YM3-251
    • Kanoh, K.; Matsuo, Y.; Adachi, K.; Imagawa, H.; Nishizawa, M.; Shizuri, Y. Mechercharmycins A and B, cytotoxic substances from marine-derived thermoactinomyces sp. YM3-251. J. Antibiot. 2005, 58, 289-292.
    • (2005) J. Antibiot. , vol.58 , pp. 289-292
    • Kanoh, K.1    Matsuo, Y.2    Adachi, K.3    Imagawa, H.4    Nishizawa, M.5    Shizuri, Y.6
  • 20
    • 0023151073 scopus 로고
    • X-ray crystal structure of ascidiacyclamide, a cytotoxic cyclic peptide from ascidian
    • Ishida, T.; Inoue, M.; Hamada, Y.; Kato, S.; Shioiri, T. X-ray crystal structure of ascidiacyclamide, a cytotoxic cyclic peptide from ascidian. J. Chem. Soc. Chem. Commun. 1987, 370-371.
    • (1987) J. Chem. Soc. Chem. Commun. , pp. 370-371
    • Ishida, T.1    Inoue, M.2    Hamada, Y.3    Kato, S.4    Shioiri, T.5
  • 22
    • 0027184402 scopus 로고
    • A marine natural product, patellamide D, reverses multidrug resistance in a human leukemic cell line
    • Williams, A.B.; Jacobs, R.S. A marine natural product, patellamide D, reverses multidrug resistance in a human leukemic cell line. Cancer Lett. 1993, 71, 97-102.
    • (1993) Cancer Lett. , vol.71 , pp. 97-102
    • Williams, A.B.1    Jacobs, R.S.2
  • 23
    • 84857775773 scopus 로고    scopus 로고
    • Telomestatin impairs glioma stem cell survival and growth through the disruption of telomeric G-quadruplex and inhibition of the proto-oncogene, c-Myb
    • Miyazaki, T.; Pan, Y.; Joshi, K.; Purohit, D.; Hu, B.; Demir, H.; Mazumder, S.; Okabe, S.; Yamori, T.; Viapiano, M.S.; et al. Telomestatin impairs glioma stem cell survival and growth through the disruption of telomeric G-quadruplex and inhibition of the proto-oncogene, c-Myb. Clin. Cancer Res. 2012, 18, 1268-1280.
    • (2012) Clin. Cancer Res. , vol.18 , pp. 1268-1280
    • Miyazaki, T.1    Pan, Y.2    Joshi, K.3    Purohit, D.4    Hu, B.5    Demir, H.6    Mazumder, S.7    Okabe, S.8    Yamori, T.9    Viapiano, M.S.10
  • 24
    • 84872872318 scopus 로고    scopus 로고
    • Telomestatin. Available online: (accessed on 1 October 2012)
    • Telomestatin. Available online: http://www.clinicaltrials.gov (accessed on 1 October 2012).
  • 25
    • 52449085116 scopus 로고    scopus 로고
    • Synthesis of natural product derivatives containing 2,4-concatenated oxazoles
    • Hernandez, D.; Riego, E.; Albericio, F.; Alvarez, M. Synthesis of natural product derivatives containing 2,4-concatenated oxazoles. Eur. J. Org. Chem. 2008, 3389-3396.
    • (2008) Eur. J. Org. Chem. , pp. 3389-3396
    • Hernandez, D.1    Riego, E.2    Albericio, F.3    Alvarez, M.4
  • 26
    • 33947132690 scopus 로고    scopus 로고
    • Synthesis of IB-01211, a cyclic peptide containing 2,4-concentrated thia-And oxazoles, vix Hantzsch macrocyclization
    • Hernandez, D.; Vilar, G.; Riego, E.; Canedo, L.M.; Cuevas, C.; Albericio, F.; Alvarez, M. Synthesis of IB-01211, a cyclic peptide containing 2,4-concentrated thia-And oxazoles, vix Hantzsch macrocyclization. Org. Lett. 2007, 9, 809-811.
    • (2007) Org. Lett. , vol.9 , pp. 809-811
    • Hernandez, D.1    Vilar, G.2    Riego, E.3    Canedo, L.M.4    Cuevas, C.5    Albericio, F.6    Alvarez, M.7
  • 28
    • 34547764254 scopus 로고    scopus 로고
    • Preparation of pentaazole containing cyclopeptides: Challenges in macrocyclization
    • Hernandez, D.; Riego, E.; Francesch, A.; Cuevas, C.; Albericio, F.; Alvarez, M. Preparation of pentaazole containing cyclopeptides: challenges in macrocyclization. Tetrahedron 2007, 63, 9862-9870.
    • (2007) Tetrahedron , vol.63 , pp. 9862-9870
    • Hernandez, D.1    Riego, E.2    Francesch, A.3    Cuevas, C.4    Albericio, F.5    Alvarez, M.6
  • 29
    • 0035900345 scopus 로고    scopus 로고
    • Probing host-selective phytoxicity: Synthesis of Destruxin B and several natural analogues
    • Ward, D.E.; Gai, Y.; Lazny, R.; Pedras, M.S.C. Probing Host-selective Phytoxicity: Synthesis of Destruxin B and several natural analogues. J. Org. Chem. 2001, 66, 7832-7840.
    • (2001) J. Org. Chem. , vol.66 , pp. 7832-7840
    • Ward, D.E.1    Gai, Y.2    Lazny, R.3    Pedras, M.S.C.4
  • 30
    • 0035900310 scopus 로고    scopus 로고
    • Total synthesis of comformationally constrained Didemnin B analogues. Replacement of N,O-dimethyltyrosine with L-1, 2, 34-tetrahydroisoquinoline and L-1234-tetrahydro-7-methoxyisoquinoline
    • Tarver, J.; Pfizenmayer, A.J.; Joullié, M.M. Total synthesis of comformationally constrained Didemnin B analogues. Replacement of N,O-dimethyltyrosine with L-1,2,3,4-tetrahydroisoquinoline and L-1,2,3,4-tetrahydro-7-methoxyisoquinoline. J. Org. Chem. 2001, 66, 7575-7587.
    • (2001) J Org Chem , vol.66 , pp. 7575-7587
    • Tarver, J.1    Pfizenmayer, A.J.2    Joullié, M.M.3
  • 31
    • 0025036824 scopus 로고
    • Total synthesis and structural investigations of didemnins A, B, and C
    • Li, W.R.; Ewing, W.R.; Harris, B.D.; Joullié, M.M. Total synthesis and structural investigations of didemnins A, B, and C. J. Am. Chem. Soc. 1990, 112, 7659-7672.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 7659-7672
    • Li, W.R.1    Ewing, W.R.2    Harris, B.D.3    Joullié, M.M.4
  • 32
    • 0027967358 scopus 로고
    • Synthesis of new didemnin B analogs for investigations of structure/biological activity relationships
    • Mayer, S.C.; Ramanjulu, J.; Vera, M.D.; Pfizenmayer, A.; Joullié, M.M. Synthesis of new didemnin B analogs for investigations of structure/biological activity relationships. J. Org. Chem. 1994, 59, 5192-5205.
    • (1994) J. Org. Chem. , vol.59 , pp. 5192-5205
    • Mayer, S.C.1    Ramanjulu, J.2    Vera, M.D.3    Pfizenmayer, A.4    Joullié, M.M.5
  • 35
    • 0035917334 scopus 로고    scopus 로고
    • Total synthesis of a conformationally constrained didemnin B analog
    • Xiao, D.; Vera, M.D.; Liang, B.; Joullié, M.M. Total synthesis of a conformationally constrained didemnin B analog. J. Org. Chem. 2001, 66, 2734-2742.
    • (2001) J. Org. Chem. , vol.66 , pp. 2734-2742
    • Xiao, D.1    Vera, M.D.2    Liang, B.3    Joullié, M.M.4
  • 36
    • 0030854642 scopus 로고    scopus 로고
    • Synthesis of a reduced ring analog of Didemnin B
    • Ramanjulu, J.; Ding, X.; Li, W.R.; Joullié, M.M. Synthesis of a reduced ring analog of Didemnin B. J. Org. Chem. 1997, 62, 4961-4969.
    • (1997) J. Org. Chem. , vol.62 , pp. 4961-4969
    • Ramanjulu, J.1    Ding, X.2    Li, W.R.3    Joullié, M.M.4
  • 37
    • 84858704374 scopus 로고    scopus 로고
    • A diversity-oriented synthesis approach to macrocycles via oxidative ring expansion
    • Kopp, F.; Stratton, C.F.; Akella, L.B.; Tan, D.S. A diversity-oriented synthesis approach to macrocycles via oxidative ring expansion. Nat. Chem. Biol. 2012, 8, 358-365.
    • (2012) Nat. Chem. Biol. , vol.8 , pp. 358-365
    • Kopp, F.1    Stratton, C.F.2    Akella, L.B.3    Tan, D.S.4
  • 38
    • 75349103837 scopus 로고    scopus 로고
    • Expedient synthesis of benzene tricarboxamide macrocycles derived from p-Aminobenzoic acid
    • Campbell, F.; Kilner, C.A.; Wilson, A.J. Expedient synthesis of benzene tricarboxamide macrocycles derived from p-Aminobenzoic acid. Tetrahedron Lett. 2010, 51, 1361-1363.
    • (2010) Tetrahedron Lett. , vol.51 , pp. 1361-1363
    • Campbell, F.1    Kilner, C.A.2    Wilson, A.J.3
  • 42
    • 29144464196 scopus 로고    scopus 로고
    • High-yielding macrocyclization conditions used in the synthesis of novel Sansalvamide A derivatives
    • Styers, T.J.; Rodriguez, R.A.; Pan, P.-S.; McAlpine, S.R. High-yielding macrocyclization conditions used in the synthesis of novel Sansalvamide A derivatives. Tetrahedron Lett. 2006, 47, 515-517.
    • (2006) Tetrahedron Lett. , vol.47 , pp. 515-517
    • Styers, T.J.1    Rodriguez, R.A.2    Pan, P.-S.3    McAlpine, S.R.4
  • 46
    • 77955430918 scopus 로고    scopus 로고
    • Histone deacetylace inhibitors: Synthesis of cyclic tetrapeptides and their triazole analogs
    • Singh, E.K.; Nazarova, L.A.; Lapera, S.A.; Alexander, L.D.; McAlpine, S.R. Histone deacetylace inhibitors: Synthesis of cyclic tetrapeptides and their triazole analogs. Tetrahedron Lett. 2010, 51, 4357-4360.
    • (2010) Tetrahedron Lett. , vol.51 , pp. 4357-4360
    • Singh, E.K.1    Nazarova, L.A.2    Lapera, S.A.3    Alexander, L.D.4    McAlpine, S.R.5
  • 48
    • 84857821949 scopus 로고    scopus 로고
    • Total synthesis of natural product trans,trans-Sanguinamide B and its structurally related conformational analogs
    • Singh, E.; Ramsey, D.M.; McAlpine, S.R. Total synthesis of natural product trans,trans-Sanguinamide B and its structurally related conformational analogs. Org. Lett. 2012, 14, 1198-1201.
    • (2012) Org. Lett. , vol.14 , pp. 1198-1201
    • Singh, E.1    Ramsey, D.M.2    McAlpine, S.R.3
  • 49
    • 73249150734 scopus 로고    scopus 로고
    • Evaluation of Di-sansalvmide A derivatives: Synthesis, structure-Activity relationship, and mechanism of action
    • Alexander, L.D.; Sellers, R.P.; Davis, M.E.; Ardi, V.C.; Johnson, V.A.; Vasko, R.C.; McAlpine, S.R. Evaluation of Di-sansalvmide A derivatives: Synthesis, structure-Activity relationship, and mechanism of action. J. Med. Chem. 2009, 52, 7927-7930.
    • (2009) J. Med. Chem. , vol.52 , pp. 7927-7930
    • Alexander, L.D.1    Sellers, R.P.2    Davis, M.E.3    Ardi, V.C.4    Johnson, V.A.5    Vasko, R.C.6    McAlpine, S.R.7
  • 52
    • 84863624300 scopus 로고    scopus 로고
    • Progress toward the synthesis of Urukthapelstatin A and two analogues
    • Pan, C.-M.; Lin, C.-C.; Kim, S.J.; Sellers, R.P.; McAlpine, S.R. Progress toward the synthesis of Urukthapelstatin A and two analogues. Tetrahedron Lett. 2012, 53, 4065-4069.
    • (2012) Tetrahedron Lett. , vol.53 , pp. 4065-4069
    • Pan, C.-M.1    Lin, C.-C.2    Kim, S.J.3    Sellers, R.P.4    McAlpine, S.R.5
  • 53
    • 79960244208 scopus 로고    scopus 로고
    • Evolution of amide bond formation
    • Joullié, M.M.; Lassen, K.M. Evolution of amide bond formation. ARKIVOC 2010. 8, 189-250.
    • (2010) ARKIVOC , vol.8 , pp. 189-250
    • Joullié, M.M.1    Lassen, K.M.2
  • 54
    • 0031888063 scopus 로고    scopus 로고
    • Fmoc/Trt-Amino acids: Comparison to Fmoc/tBu-Amino acids in peptide synthesis
    • Barlos, K.; Gatos, D.; Koutsogianni, S. Fmoc/Trt-Amino acids: Comparison to Fmoc/tBu-Amino acids in peptide synthesis. J. Pept. Res. 1998, 51, 194-200.
    • (1998) J. Pept. Res. , vol.51 , pp. 194-200
    • Barlos, K.1    Gatos, D.2    Koutsogianni, S.3


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