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Volumn 66, Issue 32, 2010, Pages 6019-6025

Binding of a hemoregulatory tetrapeptide by a bis-guanidinium crown ether

Author keywords

[No Author keywords available]

Indexed keywords

ALANYLSERYLASPARTYLLYSYLPROLINE; AMMONIA; AMMONIUM CARBONATE; AMPHOLYTE; BIS GUANIDINIUM; CARBOXYLIC ACID DERIVATIVE; CROWN ETHER; DICARBOXYLIC ACID; DIMETHYL 14 [2 [3,5 BIS [1 (PYRROL 2 CARBONYL)GUANIDINOMETHYL]BENZAMIDO] ETHYL] 6,7,9,10,13,14,15,16,18,19,21,22 DODECAHYDRO 12H 5,8,11,17,20,23 HEXAOXA 14 AZA BENZOCYCLOHENEICOSENE 2,3 DICARBOXYLATE; DIMETHYL 14 [2 [3,5 BIS [1 (TERT BUTYLOXYCARBONYL)3 (PYRROL 2 CARBONYL)GUANIDINO METHYL)BENZAMIDO] ETHYL]6,7,9,10,13,14,15,16,18,19,21,22 DODECAHYDRO 1H 5,8,11,17,20,23 HEXAOXA 14 AZA BENZOCYCLOHENEICOSENE 2,3 DICARBOXYLATE; GUANIDINE; METHYL 3,5 BIS [1 (TERT BUTYLOXYCARBONYL) 3 (PYRROL 2 CARBONYL)GUANIDINO METHYL]BENZOATE; SODIUM 3,5 BIS [1 (TERT BUTYLOXYCARBONYL) 3 (PYRROL 2 CARBONYL)GUANIDINO METHYL]BENZOATE; TETRAPEPTIDE; UNCLASSIFIED DRUG;

EID: 77955425117     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.06.024     Document Type: Article
Times cited : (15)

References (42)
  • 25
    • 77955424894 scopus 로고    scopus 로고
    • Note
    • The cyclised by-product 1-oxo-1,2-dihydro-pyrrolo[1,2-c]imidazol-3- ylidene is formed using Hg(II) as catalyst in DMF.
  • 26
    • 77955419037 scopus 로고    scopus 로고
    • Heterogeneous reaction leads to increased amounts of the side product 1-oxo-1,2-dihydro-pyrrolo[1,2-c]imidazol-3-ylidene.
    • Heterogeneous reaction leads to increased amounts of the side product 1-oxo-1,2-dihydro-pyrrolo[1,2-c]imidazol-3-ylidene.
  • 27
    • 77955427943 scopus 로고    scopus 로고
    • Note
    • 4 as the reference compound (Φ=0.546).
  • 28
    • 77955419952 scopus 로고    scopus 로고
    • Note
    • a value of the pyrrole guanidinium groups is 6.5. See Supplementary data.
  • 29
    • 77955413402 scopus 로고    scopus 로고
    • In pure methanol the crown ether binds this ammonium guest weakly (log K (2)=2.2 and log K (6b)=2.3)
    • In pure methanol the crown ether binds this ammonium guest weakly (log K (2)=2.2 and log K (6b)=2.3).
  • 30
    • 77955413084 scopus 로고    scopus 로고
    • Note
    • Sodium is not bound by the crown ether (21-crown-7). Even if a 2000 fold excess is added in aqueous methanol no change in luminescence can be observed.
  • 32
    • 77955417833 scopus 로고    scopus 로고
    • Note
    • The amino acid Glu is used instead of Asp due to synthetic reasons. The structural difference should not influence the selectivity and binding strength to a large extent.
  • 39
    • 77955429780 scopus 로고    scopus 로고
    • Note
    • The free base was prepared from the hydrochloride by shaking its chloroform solution several times with an aqueous solution of potassium carbonate (2 M). The combined aqueous phases were re-extracted three times with chloroform.
  • 40
    • 0007161484 scopus 로고
    • The splitting of some signals in the spectrum indicates the presence of unequal populations of two conformers at room temperature. This observation caused by hindered rotation in the molecule is literature known: D.R. Dalton, K.E. Ramey, H.J. Gisler Jr., L.J. Lendvay, and A. Abraham J. Am. Chem. Soc. 91 1969 6367 6370 and literature therein
    • (1969) J. Am. Chem. Soc. , vol.91 , pp. 6367-6370
    • Dalton, D.R.1    Ramey, K.E.2    Gisler, Jr.H.J.3    Lendvay, L.J.4    Abraham, A.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.