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Volumn 118, Issue 7, 1996, Pages 1595-1607

Protonated sapphyrins. Highly effective phosphate receptors

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE PHOSPHATE; PHOSPHATE; PHOSPHONIC ACID DERIVATIVE; PORPHYRIN DERIVATIVE; SAPPHYRIN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0030002361     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9529605     Document Type: Article
Times cited : (159)

References (112)
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    • and references therein
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    • (1985) Top. Curr. Chem. , vol.128 , pp. 113-141
    • Kimura, E.1
  • 13
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    • and references therein
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    • (1986) Top. Curr. Chem. , vol.132 , pp. 101-133
    • Schmidtchen, F.P.1
  • 68
    • 0004214293 scopus 로고
    • Academic Press: New York
    • (a) Dolphin, D., Ed. The Porphyrins; Academic Press: New York, 1978; Vols. I-VII.
    • (1978) The Porphyrins , vol.1-7
    • Dolphin, D.1
  • 72
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    • Falk, J. E., Lemberg, R., Morton, R. K., Eds.; Pergamon Press: New York
    • (c) Dempsey, B.; Lowe, M. B.; Phillips, J. N. In Haematin Enzymes; Falk, J. E., Lemberg, R., Morton, R. K., Eds.; Pergamon Press: New York, 1961; Vol. 1. pp 29-40.
    • (1961) Haematin Enzymes , vol.1 , pp. 29-40
    • Dempsey, B.1    Lowe, M.B.2    Phillips, J.N.3
  • 73
    • 0003946851 scopus 로고
    • Elsevier Publishing Company: New York
    • a values using Tween 20 are lower. Analogous spectroscopic titrations with sapphyrin 1 yielded inconclusive results because changes in absorption as a function of pH could not be clearly assigned to protonated and free-base sapphyrin species This situation is unlike the case found with porphyrins, where well-defined absorption patterns in the Q-band region can be used in the identification of such porphyrin-based species.
    • (1964) Porphyrins and Metalloporphyrins , pp. 27-30
    • Falk, J.E.1
  • 103
    • 13344273527 scopus 로고    scopus 로고
    • note
    • 17b visible spectroscopy provides a very convenient means of assessing sapphyrin-sapphvrin aggregation: The characteristic Soret-type absorbance band of sapphyrin (free-base, mono- or diprotonated) appears at 445-450 nm when it is monomeric. at ca. 420 nm when it is dimeric. and at ca. 400 nm when it is more highly aggregated.
  • 105
    • 13344254351 scopus 로고    scopus 로고
    • 4
    • 4
  • 106
    • 13344271944 scopus 로고    scopus 로고
    • note
    • The magnitude of the shifts was always greater in the case of phenylphosphonate than in the case of the dihydrogen phosphate which we interpret in terms of better binding interactions with phenylphosphonate. These we suggest could result from an extra stabilization arising from favorable π-π stacking effects present in the case of the phenylphosphonate complex and would be analogous to those seen in the solid-state structure of the 2 1 phenyl phosphate-sapphyrin complex shown in Figure 4.
  • 109
    • 13344292651 scopus 로고    scopus 로고
    • note
    • 4 that are displaced upfield by only 3.23 and 2.93 ppm. respectively, relative to those of the free-acid form.
  • 110
    • 13344251532 scopus 로고    scopus 로고
    • note
    • Many other titrations were also carried out using a range of other phosphate-sapphyrin mixtures with both compounds being m sarious protonation states, e.g., free-base, mono- and diprotonated sapphyrin. free-acid, mono- and dibasic phosphate acids. See Supporting Information
  • 111
    • 13344251533 scopus 로고    scopus 로고
    • In these experiments, the sapphyrin methine protons could also be monitored. As expected, these sets of signals also moved to higher field as complexation was allowed to occur
    • In these experiments, the sapphyrin methine protons could also be monitored. As expected, these sets of signals also moved to higher field as complexation was allowed to occur.
  • 112
    • 11644294419 scopus 로고
    • Alberts, A., Badger, G. M., Shoppee, C. W., Eds : Academic Press. Inc New York
    • a determinations. A nonionic detergent was employed in this study to avoid difficulties involving the precipitation of the neutral macrocycle at high pH. Interestingly, the monocation of sapphyrin 1 is clearly stable under these conditions, a phenomenon that, to the best of our know ledge, has not been observable with octaalkyl porphyrins in the presence of nonionic detergents. See. Phillips, J. N. In Current Trends in Heterocyclic Chemistry: Alberts, A., Badger, G. M., Shoppee, C. W., Eds : Academic Press. Inc New York, 1958. pp 30-39
    • (1958) Current Trends in Heterocyclic Chemistry , pp. 30-39
    • Phillips, J.N.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.