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Volumn 72, Issue 6, 1999, Pages 1351-1364

A 12-porphyrin system: Syntheses of peptide porphyrins with multiple histidines and the aggregation behavior in the presence of hemin

Author keywords

[No Author keywords available]

Indexed keywords

HEMIN; HISTIDINE; PEPTIDE DERIVATIVE; PEPTIDE PORPHYRIN; PORPHYRIN; UNCLASSIFIED DRUG;

EID: 0033033412     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.72.1351     Document Type: Article
Times cited : (4)

References (68)
  • 28
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    • note
    • 2, from which the stabilization free energy on the ice-shell liquidation was derived according to Ref. 26.
  • 29
    • 0013576661 scopus 로고    scopus 로고
    • note
    • The detail will be reported elsewhere.
  • 30
    • 0023977089 scopus 로고
    • Molecular graphics images were produced using the MidasPlus software system from the Computer Graphics Laboratory, University of California, San Francisco: T. E. Ferrin, C. C. Huang, L. E. Jarvis, and R. Langridge, J. Mol. Graphics, 6, 13 (1988).
    • (1988) J. Mol. Graphics , vol.6 , pp. 13
    • Ferrin, T.E.1    Huang, C.C.2    Jarvis, L.E.3    Langridge, R.4
  • 32
    • 0013627692 scopus 로고    scopus 로고
    • note
    • Due to its impossibility of purification of intermediates, the solid-phase peptide synthesis is inferior to the liquid phase method to make sure the preparation of high purity product (Ref. 24). Furthermore, the purification of protected peptide is generally difficult because of its low solubility (Ref. 32), even if the peptide is carefully cleaved from the resin without deprotection of the side chains.
  • 35
    • 0013606807 scopus 로고    scopus 로고
    • note
    • 2N-n, for the phenacyl and Boc cleaved forms, respectively, where n means the substance number 1 to 6. For example, 6-OH equals Boc-Glu(OBzl)-Glu(OBzl)-Ala-Leu-Glu(OBzl)-Lys-(ClZ)-His-Glu(OBzl)-Lys(ClZ)-Ala- Leu-Glu(OBzl)-Lys-(ClZ)-His-Glu(OBzl)-Lys(ClZ)-OH.
  • 37
    • 0013576662 scopus 로고    scopus 로고
    • note
    • 4, the application of Zn powder caused a fast remarkable bleaching of this compound.
  • 46
    • 0013579274 scopus 로고    scopus 로고
    • note
    • The phenacyl esters of 1,4,5, and 6 were efficiently removed by Zn/90% acetic acid.
  • 47
    • 0013612009 scopus 로고    scopus 로고
    • note
    • a) This side reaction gave only one by-product which showed the same mass number as 6, which shows the possibility of the racemization of 6 at the coupling.
  • 48
    • 0013579275 scopus 로고    scopus 로고
    • note
    • b) Histidine easily racemizes via the steric interaction of the imidazole group and the carboxyl group, or the elimination of the a-hydrogen by the imidazole group (Refs. 47 and 48). The molecular modeling of peptide fragments 3-OH and 5-OH showed that the imidazole groups of their histidines, which are placed on the third residues from the carboxyl termini, can take close positions to their C-terminal amino acids, which might cause the similar racemization effect on the C-terminal residues.
  • 53
    • 0013606809 scopus 로고    scopus 로고
    • note
    • 80% yield was achieved at this point.
  • 56
    • 0013607579 scopus 로고    scopus 로고
    • note
    • The aqueous acetonitrile solution containing TEA or AcOH achieved good separation, but the TEA-containing eluent also achieved a good result with less amount of water. This was advantageous to treat the compound, because the mixing of water decreased the solubility of compound.
  • 60
    • 0013627504 scopus 로고    scopus 로고
    • note
    • In the presence of 6-OH, such instability of the porphyrin fragment was not observed.
  • 64
    • 0013606811 scopus 로고    scopus 로고
    • note
    • -1 (Ref. 63).
  • 68
    • 0013607070 scopus 로고    scopus 로고
    • note
    • 1H NMR, FAB MS, and elemental analysis were reported in the Ref. 20.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.