메뉴 건너뛰기




Volumn 17, Issue 22, 2007, Pages 6286-6289

Catalysis of imido group hydrolysis in a maleimide conjugate

Author keywords

Bioconjugation; Catalysis; Chromate; Hydrolysis; Imido group; Malemide; Molybdate; Oxometalate; Succinimide

Indexed keywords

CHROMIC ACID; DIMETHYLAMINE; IMIDE; MALEIMIDE; MOLYBDIC ACID; PYRIDINE DERIVATIVE; THIOL DERIVATIVE; TUNGSTEN;

EID: 35148873679     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.09.002     Document Type: Article
Times cited : (69)

References (41)
  • 21
    • 35148814414 scopus 로고    scopus 로고
    • Nektar Therapeutics AL, Corp., World Patent WO 2004/06095 (2004).
  • 22
    • 0348099030 scopus 로고    scopus 로고
    • Succinimides that form in polypeptide chains by the cyclization of asparagine residues are known to undergo spontaneous hydrolysis to form isoaspartate residues. For a review, see:
    • Succinimides that form in polypeptide chains by the cyclization of asparagine residues are known to undergo spontaneous hydrolysis to form isoaspartate residues. For a review, see:. Clark S. Ageing Res. Rev. 2 (2003) 263
    • (2003) Ageing Res. Rev. , vol.2 , pp. 263
    • Clark, S.1
  • 27
    • 35148828571 scopus 로고    scopus 로고
    • Rutkoski, T. J.; Raines, R. T. unpublished results.
  • 28
    • 35148840993 scopus 로고    scopus 로고
    • Underbakke, E. S.; Kiessling, L. L. personal communication.
  • 31
    • 35148874621 scopus 로고    scopus 로고
    • note
    • 4: C, 51.41; H, 4.32; N, 10.00; S, 11.44; O, 22.83. Found: C, 51.76; H, 4.26; N, 9.96; S, 11.81; O, 22.21.
  • 36
    • 35148868649 scopus 로고    scopus 로고
    • note
    • 2 is the second-order rate constant.
  • 37
    • 35148886269 scopus 로고    scopus 로고
    • note
    • Succinimide 2 (382 μL of a 1.65 mM solution in acetonitrile) was added to a solution (20 mL) of 50 mM Hepes-NaOH buffer at pH 7.5 containing catalyst (0.10 M) and NaCl (0.10 M). The reaction mixture was stirred for 2 h and extracted with ethyl acetate (2 × 20 mL). The organic layer was concentrated under reduced pressure, and the residue was analyzed by C18 HPLC using a linear gradient of water (80-20% v/v) in acetonitrile containing TFA (0.1% v/v) over 50 min. Hydrolyzed succinimide 2 eluted in two peaks at 40 min; intact succinimide 2 eluted at 45 min. To compare molybdate and chromate as catalysts, reactions were performed on 90-mL scale, and 20-mL aliquots were removed at four time points and subjected to HPLC analysis.
  • 38
    • 35148899590 scopus 로고    scopus 로고
    • note
    • 5, 321.06; found, 321.00.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.