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Volumn 9, Issue 1, 2008, Pages 33-37

Head-to-tail cyclized cystine-knot peptides by a combined recombinant and chemical route of synthesis

Author keywords

Cyclic peptides; Cystine knot miniproteins; Hydrazones; Inhibitors; Macrocyclization; Protein modifications

Indexed keywords

CONOTOXIN; CYCLOPEPTIDE; CYCLOTIDE; CYSTEINE; GAMMA LACTONE DERIVATIVE; HYBRID PROTEIN; HYDRAZONE DERIVATIVE; ION CHANNEL; METHIONINE; PEPTIDE DERIVATIVE; PERIODATE SODIUM; RECOMBINANT PROTEIN; SPIDER VENOM; TRYPTASE;

EID: 38149082114     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.200700452     Document Type: Article
Times cited : (27)

References (71)
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    • "Cyclopeptides as Macrocyclic Host Molecules for Charged Guests", S. Kubik in Highlights in Bioorganic Chemistry: Methods and Applications (Eds.: C. Schmuck, H. Wennemers), Wiley-VCH, Weinheim, 2004;
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    • Intein-mediated protein splicing for macrocycle formation of cysteine knot peptides by use of mini-inteins (New England Biolabs) has proven difficult in our hands. Cyclic peptides were obtained, but in unacceptable low yields (H. U. Schmoldt, unpublished observations). Relatively low yields were also reported by J. A. Camarero, R. H. Kimura, Y.-H. Woo, A. Shekhtman, J. Cantor, ChemBioChem 2007, 8, 1363-1366.
    • Intein-mediated protein splicing for macrocycle formation of cysteine knot peptides by use of mini-inteins (New England Biolabs) has proven difficult in our hands. Cyclic peptides were obtained, but in unacceptable low yields (H. U. Schmoldt, unpublished observations). Relatively low yields were also reported by J. A. Camarero, R. H. Kimura, Y.-H. Woo, A. Shekhtman, J. Cantor, ChemBioChem 2007, 8, 1363-1366.
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    • Chemical Ligation, P. Dawson in Houben Weyl, Methods of Organic Chemistry, V. E22a, Synthesis of Peptides and Peptidomimetics (Ed.; M. Goodman, A. Felix, L. Moroder, C. Toniolo), Thieme, Stuttgart, 2002, 621-641.
    • "Chemical Ligation", P. Dawson in Houben Weyl, Methods of Organic Chemistry, V. E22a, Synthesis of Peptides and Peptidomimetics (Ed.; M. Goodman, A. Felix, L. Moroder, C. Toniolo), Thieme, Stuttgart, 2002, 621-641.
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    • Alternative routes to the selective oxidation of N-terminal amino acids through a biomimetic transamination reaction have been described recently: J. M. Gilmore, R. A. Scheck, A. P. Esser-Kahn, N. S. Joshi, M. B. Francis, Angew. Chem. 2006, 118, 5433-5437;
    • Alternative routes to the selective oxidation of N-terminal amino acids through a biomimetic transamination reaction have been described recently: J. M. Gilmore, R. A. Scheck, A. P. Esser-Kahn, N. S. Joshi, M. B. Francis, Angew. Chem. 2006, 118, 5433-5437;
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    • Yields are based on isolated material and were calculated from material weight after RP-HPLC and extensive lyophilization
    • Yields are based on isolated material and were calculated from material weight after RP-HPLC and extensive lyophilization.
  • 66
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    • 2. Spectral characteristics of hydrazones have been described in: Yu. P. Kitaev, B. I. Buzykin, T. V. Troepol'skaya, Russ. Chem. Rev. 1970, 39, 441-456;
    • 2. Spectral characteristics of hydrazones have been described in: Yu. P. Kitaev, B. I. Buzykin, T. V. Troepol'skaya, Russ. Chem. Rev. 1970, 39, 441-456;
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    • 3 as it has been reported that reduction of hydrazone bonds can induce precipitation of the target macromolecule: S. L. Rakestraw, R. G. Tompkins, M. L. Yarmush, Bioconjugate Chem. 1990, 7, 212-221.
    • 3 as it has been reported that reduction of hydrazone bonds can induce precipitation of the target macromolecule: S. L. Rakestraw, R. G. Tompkins, M. L. Yarmush, Bioconjugate Chem. 1990, 7, 212-221.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.