메뉴 건너뛰기




Volumn 13, Issue 2, 2011, Pages 107-111

Solid-phase synthesis of tris-benzamides as α-helix mimetics

Author keywords

helix mimetics; Protein protein interaction; Solid phase synthesis; Tris benzamide scaffold

Indexed keywords

BENZAMIDE DERIVATIVE; PROTEIN;

EID: 79955370176     PISSN: 21568952     EISSN: None     Source Type: Journal    
DOI: 10.1021/co100056c     Document Type: Article
Times cited : (34)

References (42)
  • 1
    • 68949119587 scopus 로고    scopus 로고
    • Assessment of helical interfaces in protein - Protein interactions
    • Jochim, A. L.; Arora, P. S. Assessment of Helical Interfaces in Protein - Protein Interactions. Mol. BioSyst. 2009, 5, 924-926.
    • (2009) Mol. BioSyst. , vol.5 , pp. 924-926
    • Jochim, A.L.1    Arora, P.S.2
  • 2
    • 0034228707 scopus 로고    scopus 로고
    • Peptide and protein recognition by designed molecules
    • Peczuh, M, W.; Hamilton, A. D. Peptide and Protein Recognition by Designed Molecules. Chem. Rev. 2000, 100, 2479-2494.
    • (2000) Chem. Rev. , vol.100 , pp. 2479-2494
    • Peczuh, M.W.1    Hamilton, A.D.2
  • 3
    • 33846662867 scopus 로고    scopus 로고
    • Synthetic non-peptide mimetics of α-helices
    • Davis, J. M.; Tsou, L. K; Hamilton, A. D. Synthetic Non-Peptide Mimetics of α-Helices. Chem. Soc. Rev. 2007, 36, 326-334.
    • (2007) Chem. Soc. Rev. , vol.36 , pp. 326-334
    • Davis, J.M.1    Tsou, L.K.2    Hamilton, A.D.3
  • 4
    • 0000478078 scopus 로고
    • Templates that induce α-helical, β-sheet, and loop conformations
    • Schneider, J. P.; Kelly, J. W. Templates That Induce α-Helical, β-Sheet, and Loop Conformations. Chem. Rev. 1995, 95, 2169-2187.
    • (1995) Chem. Rev. , vol.95 , pp. 2169-2187
    • Schneider, J.P.1    Kelly, J.W.2
  • 5
    • 0037059026 scopus 로고    scopus 로고
    • Recent advances in helix-coil theory
    • DOI 10.1016/S0301-4622(02)00170-9, PII S0301462202001709
    • Doig, A. J. Recent Advances in Helix-Coil Theory. Biophys. Chem. 2002, 101-102, 281-293. (Pubitemid 35462053)
    • (2002) Biophysical Chemistry , vol.101-102 , pp. 281-293
    • Doig, A.J.1
  • 6
    • 17244364283 scopus 로고    scopus 로고
    • Proteases universally recognize beta strands in their active sites
    • DOI 10.1021/cr040669e
    • Tyndall, J. D. A.; Nall, T.; Fairlie, D. P. Proteases Universally Recognize Beta Strands in Their Active Sites. Chem. Rev. 2005, 105, 973-999. (Pubitemid 40527381)
    • (2005) Chemical Reviews , vol.105 , Issue.3 , pp. 973-999
    • Tyndall, J.D.A.1    Nall, T.2    Fairlie, D.P.3
  • 10
    • 0000953716 scopus 로고
    • Multicyclic polypeptide model compounds. 2. Synthesis and conformational properties of a highly α-helical uncosapeptide constrained by three side-chain to side-chain lactam bridges
    • (a) Ösapay, G.; Taylor, J. W. Multicyclic Polypeptide Model Compounds. 2. Synthesis and Conformational Properties of a Highly α-Helical Uncosapeptide Constrained by Three Side-Chain to Side-Chain Lactam Bridges. J. Am. Chem. Soc. 1992, 114, 6966-6973.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 6966-6973
    • Ösapay, G.1    Taylor, J.W.2
  • 11
    • 0031027124 scopus 로고    scopus 로고
    • A general method for constraining short peptides to an α-helical conformation
    • DOI 10.1021/ja9611654, PII S0002786396011651
    • (b) Phelan, J. C.; Skelton, N. J.; Braisted, A. C.; McDowell, R. S. A General Method for Constraining Short Peptides to an α-Helical Conformation. J. Am. Chem. Soc. 1997, 119, 455-460. (Pubitemid 27086532)
    • (1997) Journal of the American Chemical Society , vol.119 , Issue.3 , pp. 455-460
    • Phelan, J.C.1    Skelton, N.J.2    Braisted, A.C.3    McDowell, R.S.4
  • 12
    • 0035855890 scopus 로고    scopus 로고
    • A new approach to search for the bioactive conformation of glucagon: Positional cyclization scanning
    • DOI 10.1021/jm010091q
    • (c) Ahn, J.-M.; Gitu, P. M.; Medeiros, M.; Swift, J. R.; Trivedi, D.; Hruby, V. J. A New Approach to Search for the Bioactive Conformation of Glucagon: Positional Cyclization Scanning. J. Med. Chem. 2001, 44, 3109-3116. (Pubitemid 32862341)
    • (2001) Journal of Medicinal Chemistry , vol.44 , Issue.19 , pp. 3109-3116
    • Ahn, J.-M.1    Gitu, P.M.2    Medeiros, M.3    Swift, J.R.4    Trivedi, D.5    Hruby, V.J.6
  • 13
    • 55749095379 scopus 로고    scopus 로고
    • Search for α-helical propensity in the receptor-bound conformation of glucagon-like peptide-1
    • (d) Murage, E.; Schroeder, J. C.; Beinborn, M.; Ahn, J.-M. Search for α-Helical Propensity in the Receptor-Bound Conformation of Glucagon-Like Peptide-1. Bioorg. Med. Chem. 2008, 16, 10106-10112.
    • (2008) Bioorg. Med. Chem. , vol.16 , pp. 10106-10112
    • Murage, E.1    Schroeder, J.C.2    Beinborn, M.3    Ahn, J.-M.4
  • 15
    • 0032542374 scopus 로고    scopus 로고
    • Highly efficient synthesis of covalently cross-linked peptide helices by ring-closing metathesis
    • DOI 10.1002/(SICI)1521-3773(19981217)37:23<3281::AID-ANIE3281>3.0. CO;2-V
    • (a) Blackwell, H. E.; Grubbs, R. H. Highly Efficient Synthesis of Covalently Cross-Linked Peptide Helices by Ring-Closing Metathesis. Angew. Chem., Int. Ed. 1998, 37, 3281-3284. (Pubitemid 29016745)
    • (1998) Angewandte Chemie - International Edition , vol.37 , Issue.23 , pp. 3281-3284
    • Blackwell, H.E.1    Grubbs, R.H.2
  • 16
    • 0034697649 scopus 로고    scopus 로고
    • An all-hydrocarbon cross-linking system for enhancing the helicity and metabolic stability of peptides [8]
    • DOI 10.1021/ja000563a
    • (b) Schafmeister, C. E.; Po, J.; Verdine, G. L. An All-Hydrocarbon Cross-Linking System for Enhancing the Helicity and Metabolic Stability of Peptides. J. Am. Chem. Soc. 2000, 122, 5891-5892. (Pubitemid 30432299)
    • (2000) Journal of the American Chemical Society , vol.122 , Issue.24 , pp. 5891-5892
    • Schafmeister, C.E.1    Po, J.2    Verdine, G.L.3
  • 17
    • 57349192372 scopus 로고    scopus 로고
    • A hydrogen bond surrogate approach for stabilization of short peptide sequences in α-helical conformation
    • (c) Patgiri, A.; Jochim, A. L.; Arora, A. S. A Hydrogen Bond Surrogate Approach for Stabilization of Short Peptide Sequences in α-Helical Conformation. Acc. Chem. Res. 2008, 41, 1289-1300.
    • (2008) Acc. Chem. Res. , vol.41 , pp. 1289-1300
    • Patgiri, A.1    Jochim, A.L.2    Arora, A.S.3
  • 18
    • 11944257538 scopus 로고
    • Secondary structure nucleation in peptides. Transition metal ion stabilized α-helices
    • Ghadiri, M. R.; Choi, C. Secondary Structure Nucleation in Peptides. Transition Metal Ion Stabilized α-Helices. J. Am. Chem. Soc. 1990, 112, 1630-1632.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 1630-1632
    • Ghadiri, M.R.1    Choi, C.2
  • 19
    • 0033611958 scopus 로고    scopus 로고
    • The hydrogen bond mimic approach: Solid-phase synthesis of a peptide stabilized as an α-helix with a hydrazone link
    • Cabezas, E.; Satterthwait, A. C. The Hydrogen Bond Mimic Approach: Solid-Phase Synthesis of a Peptide Stabilized as an α-Helix with a Hydrazone Link. J. Am. Chem. Soc. 1999, 121, 3862-3875.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 3862-3875
    • Cabezas, E.1    Satterthwait, A.C.2
  • 20
    • 41549141350 scopus 로고    scopus 로고
    • Atomic structure of a short α-helix stabilized by a main chain hydrogen-bond surrogate
    • DOI 10.1021/ja077704u
    • Liu, J.; Wang, D.; Zheng, Q.; Lu, M.; Arora, P. S. Atomic Structure of a Short α-Helix Stabilized by a Main Chain Hydrogen-Bond Surrogate. J. Am. Chem. Soc. 2008, 130, 4334-4337. (Pubitemid 351466428)
    • (2008) Journal of the American Chemical Society , vol.130 , Issue.13 , pp. 4334-4337
    • Liu, J.1    Wang, D.2    Zheng, Q.3    Lu, M.4    Arora, P.S.5
  • 21
    • 57349134690 scopus 로고    scopus 로고
    • Foldamers with heterogeneous backbones
    • (a) Horne, W. S.; Gellman, S. H. Foldamers with Heterogeneous Backbones. Acc. Chem. Res. 2008, 41, 1399-1408.
    • (2008) Acc. Chem. Res. , vol.41 , pp. 1399-1408
    • Horne, W.S.1    Gellman, S.H.2
  • 22
    • 57149097169 scopus 로고    scopus 로고
    • β-peptidic peptidomimetics
    • (b) Seebach, D.; Gardiner, J. β-Peptidic Peptidomimetics. Acc. Chem. Res. 2008, 41, 1366-1375.
    • (2008) Acc. Chem. Res. , vol.41 , pp. 1366-1375
    • Seebach, D.1    Gardiner, J.2
  • 23
    • 35748977122 scopus 로고    scopus 로고
    • Design and synthesis of α-helical peptides and mimetics
    • DOI 10.1039/b710425a
    • Garner, J.; Harding, M. M. Design and Synthesis of α-Helical Peptides and Mimetics. Org. Biomol. Chem. 2007, 5, 3577-3585. (Pubitemid 350041641)
    • (2007) Organic and Biomolecular Chemistry , vol.5 , Issue.22 , pp. 3577-3585
    • Garner, J.1    Harding, M.M.2
  • 24
    • 0029972738 scopus 로고    scopus 로고
    • The design of dipeptide helical mimetics: The synthesis, tachykinin receptor affinity and conformational analysis of 1,1,6-trisubstituted indanes
    • Horwell, D. C.; Howson, W.; Ratcliffe, G. S.; Willems, H. M. G. The Design of Dipeptide Helical Mimetics: The Synthesis, Tachykinin Receptor Affinity and Conformational Analysis of 1,1,6-Trisubstituted Indanes. Bioorg. Med. Chem. 1996, 4, 33-42.
    • (1996) Bioorg. Med. Chem. , vol.4 , pp. 33-42
    • Horwell, D.C.1    Howson, W.2    Ratcliffe, G.S.3    Willems, H.M.G.4
  • 25
    • 0034801374 scopus 로고    scopus 로고
    • Toward proteomimetics: Terphenyl derivatives as structural and functional mimics of extended regions of an α-helix [18]
    • DOI 10.1021/ja0025548
    • (a) Orner, B. P.; Ernst, J. T.; Hamilton, A. D. Toward Proteomimetics: Terphenyl Derivatives as Structural and Functional Mimics of Extended Regions of an α-Helix. J. Am. Chem. Soc. 2001, 123, 5382-5383. (Pubitemid 32910693)
    • (2001) Journal of the American Chemical Society , vol.123 , Issue.22 , pp. 5382-5383
    • Orner, B.P.1    Ernst, J.T.2    Hamilton, A.D.3
  • 28
    • 0037415861 scopus 로고    scopus 로고
    • Design and application of an α-helix-mimetic scaffold based on an oligoamide-foldamer strategy: Antagonism of the Bak BH3/Bcl-xL complex
    • DOI 10.1002/anie.200390154
    • Ernst, J. T.; Becerril, J.; Park, H. S.; Yin, H.; Hamilton, A. D. Design and Application of an α-Helix-Mimetic Scaffold Based on an Oligoamide-Foldamer Strategy: Antagonism of the Bak BH3/Bcl-xL Complex. Angew. Chem., Int. Ed. 2003, 42, 535-539. (Pubitemid 36232248)
    • (2003) Angewandte Chemie - International Edition , vol.42 , Issue.5 , pp. 535-539
    • Ernst, J.T.1    Becerril, J.2    Park, H.S.3    Yin, H.4    Hamilton, A.D.5
  • 29
    • 33745737798 scopus 로고    scopus 로고
    • Synthesis and evaluation of α-helix mimetics based on a trans-fused polycyclic ether: Sequence-selective binding to aspartate pairs in α-helical peptides
    • Oguri, H.; Tanabe, S.; Oomura, A.; Umetsu, M.; Hirama, M. Synthesis and Evaluation of α-Helix Mimetics Based on a Trans-Fused Polycyclic Ether: Sequence-Selective Binding to Aspartate Pairs in α-Helical Peptides. Tetrahedron Lett. 2006, 47, 5801-5805.
    • (2006) Tetrahedron Lett. , vol.47 , pp. 5801-5805
    • Oguri, H.1    Tanabe, S.2    Oomura, A.3    Umetsu, M.4    Hirama, M.5
  • 30
    • 34247138372 scopus 로고    scopus 로고
    • Facile synthesis of benzamides to mimic an α-helix
    • DOI 10.1016/j.tetlet.2007.03.108, PII S0040403907005631
    • (a) Ahn, J.-M.; Han, S.-Y. Facile Synthesis of Benzamides to Mimic an α-Helix. Tetrahedron Lett. 2007, 48, 3543-3547. (Pubitemid 46590196)
    • (2007) Tetrahedron Letters , vol.48 , Issue.20 , pp. 3543-3547
    • Ahn, J.-M.1    Han, S.-Y.2
  • 32
    • 57049188285 scopus 로고    scopus 로고
    • Controlling curvature in a family of oligoamide α-helix mimetics
    • (c) Saraogi, I.; Incarvito, C. D.; Hamilton, A. D. Controlling Curvature in a Family of Oligoamide α-Helix Mimetics. Angew. Chem., Int. Ed. 2008, 47, 9691-9694.
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 9691-9694
    • Saraogi, I.1    Incarvito, C.D.2    Hamilton, A.D.3
  • 34
    • 34848921166 scopus 로고    scopus 로고
    • Synthesis of pyridazine-based scaffolds as α-helix mimetics
    • Volonterio, A.; Moisan, L.; Rebek, J., Jr Synthesis of Pyridazine-Based Scaffolds as α-Helix Mimetics. Org. Lett. 2007, 9, 3733-3736.
    • (2007) Org. Lett. , vol.9 , pp. 3733-3736
    • Volonterio, A.1    Moisan, L.2    Rebek, Jr.J.3
  • 35
    • 45849130968 scopus 로고    scopus 로고
    • Synthesis and structure of 1,4-dipiperazino benzenes: Chiral terphenyl-type peptide helix mimetics
    • Maity, P; König, B. Synthesis and Structure of 1,4-Dipiperazino Benzenes: Chiral Terphenyl-type Peptide Helix Mimetics. Org. Lett. 2008, 10, 1473-1476.
    • (2008) Org. Lett. , vol.10 , pp. 1473-1476
    • Maity, P.1    König, B.2
  • 37
    • 70350192270 scopus 로고    scopus 로고
    • Novel amphiphilic α-helix mimetics based on a bis-benzamide scaffold
    • Marimganti, S.; Cheemala, M. N.; Ahn, J.-M. Novel Amphiphilic α-Helix Mimetics Based on a Bis-benzamide Scaffold. Org. Lett. 2009, 11, 4418-4421.
    • (2009) Org. Lett. , vol.11 , pp. 4418-4421
    • Marimganti, S.1    Cheemala, M.N.2    Ahn, J.-M.3
  • 38
    • 0347009734 scopus 로고
    • The role of weight of acyl in the migration from nitrogen to oxygen. II
    • (a) Raiford, L. C.; Couture, J. R. The Role of Weight of Acyl in the Migration from Nitrogen to Oxygen. II. J. Am. Chem. Soc. 1924, 46, 2305-2318.
    • (1924) J. Am. Chem. Soc. , vol.46 , pp. 2305-2318
    • Raiford, L.C.1    Couture, J.R.2
  • 39
    • 2342624833 scopus 로고
    • The migration of acetyl and benzoyl groups in o-aminophenol
    • (b) LeRosen, A. L.; Smith, E. D. The Migration of Acetyl and Benzoyl Groups in o-Aminophenol. J. Am. Chem. Soc. 1948, 70, 2705-2709.
    • (1948) J. Am. Chem. Soc. , vol.70 , pp. 2705-2709
    • LeRosen, A.L.1    Smith, E.D.2
  • 40
    • 0025767755 scopus 로고
    • 2-chlorotrityl chloride resin: Studies on anchoring of Fmoc-amino acids and peptide cleavage
    • Barlos, K.; Chatzi, O.; Gatos, D.; Stavropoulos, G. 2-Chlorotrityl Chloride Resin: Studies on Anchoring of Fmoc-Amino Acids and Peptide Cleavage. Int. J. Pept. Protein Res. 1991, 37, 513-520.
    • (1991) Int. J. Pept. Protein Res. , vol.37 , pp. 513-520
    • Barlos, K.1    Chatzi, O.2    Gatos, D.3    Stavropoulos, G.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.