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Volumn 48, Issue 35, 2009, Pages 6443-6447

Rotaxane-based propeptides: protection and enzymatic release of a bioactive pentapeptide

Author keywords

Delivery systems; Peptides; Prodrugs; Rotaxanes; Supramolecular chemistry

Indexed keywords

DELIVERY SYSTEMS; GLYCOSIDASES; HUMAN PLASMAS; MACROCYCLES; POOR STABILITY; PRODRUGS; PROPEPTIDES; ROTAXANES;

EID: 70349913585     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200903215     Document Type: Article
Times cited : (113)

References (69)
  • 7
    • 41049086346 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 2222-2226;
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 2222-2226
  • 9
    • 39749150344 scopus 로고    scopus 로고
    • Chem. Soc. 2008, 130, 2382-2383;
    • (2008) Chem. Soc. , vol.130 , pp. 2382-2383
  • 14
    • 34547202931 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 5528-5531;
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 5528-5531
  • 17
    • 33746300518 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 1596-1599.
    • (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 1596-1599
  • 35
    • 4544231480 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2004, 43, 3260-3264;
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 3260-3264
  • 37
    • 21044434147 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 3062-3067.
    • (2005) Angew. Chem. Int. Ed , vol.44 , pp. 3062-3067
  • 39
    • 70349950371 scopus 로고    scopus 로고
    • note
    • This is likely a result of the folding of the thread through strong intramolecular hydrogen bonding in the nonpolar solvents used to promote hydrogen bond-template rotaxane formation. Yields of rotaxanes from related pentapeptide threads attempted in our laboratory were typically less than 1 %.
  • 45
    • 0042530480 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2003, 42, 3379-3383;
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 3379-3383
  • 56
    • 33749843662 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 6574-6577;
    • (2006) Angew. Chem. Int. Ed , vol.45 , pp. 6574-6577
  • 69
    • 70349950356 scopus 로고    scopus 로고
    • Intermediates 8 and 9 are only stable for a few minutes at pH 7 at 37°C However, they survive for hours at pH2 at room temperature (the equilibrium between the phenol and phenolate forms is shifted toward the phenol and elimination occurs only slowly). In the gal-catalyzed reactions, aliquots were withdrawn from the reaction medium and diluted with a solution of trifluoroacetic acid (to pH 2) before being injected into the HPLC apparatus with the mobile phase buffered at pH 2 (see the Supporting Information).
    • Intermediates 8 and 9 are only stable for a few minutes at pH 7 at 37°C However, they survive for hours at pH2 at room temperature (the equilibrium between the phenol and phenolate forms is shifted toward the phenol and elimination occurs only slowly). In the gal-catalyzed reactions, aliquots were withdrawn from the reaction medium and diluted with a solution of trifluoroacetic acid (to pH 2) before being injected into the HPLC apparatus with the mobile phase buffered at pH 2 (see the Supporting Information).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.