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Volumn 122, Issue 35, 2000, Pages 8413-8420

The molecular basis for pyrimidine-selective DNA binding: Analysis of calicheamicin oligosaccharide derivatives by capillary electrophoresis

Author keywords

[No Author keywords available]

Indexed keywords

CALICHEAMICIN; CALICHEAMICIN DERIVATIVE; DNA; IODINE; OLIGOSACCHARIDE; PYRIMIDINE;

EID: 0033828499     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000519v     Document Type: Article
Times cited : (18)

References (56)
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    • Iodine and the ethyl group have similar values in Taft's steric scale (see: March, J. Advanced Organic Chemistry; John Wiley and Sons: New York, 1992; p 285, and references therein). Sulfur is isosteric with methylene. For example, see Mislow's determination of the absolute configuration of α-lipoic acid (Mislow, K. and Meluch, W. C. J. Am. Chem. Soc. 1956, 78, 5920-5923) and the formation of similar polymorphic crystal forms of D,L-methionine and D,L-norleucine (see Dalhus, B. and Gorbitz, C. H. Acta Crystallogr., Sect. C (Cs. Str. Comm.) 1999, 55, 1105-1112, and references therein). Therefore, the replacement of iodine by the methylthio functionality is expected to result in the presentation of a comparable steric surface on the aromatic ring.
    • (1992) Advanced Organic Chemistry , pp. 285
    • March, J.1
  • 30
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    • Iodine and the ethyl group have similar values in Taft's steric scale (see: March, J. Advanced Organic Chemistry; John Wiley and Sons: New York, 1992; p 285, and references therein). Sulfur is isosteric with methylene. For example, see Mislow's determination of the absolute configuration of α-lipoic acid (Mislow, K. and Meluch, W. C. J. Am. Chem. Soc. 1956, 78, 5920-5923) and the formation of similar polymorphic crystal forms of D,L-methionine and D,L-norleucine (see Dalhus, B. and Gorbitz, C. H. Acta Crystallogr., Sect. C (Cs. Str. Comm.) 1999, 55, 1105-1112, and references therein). Therefore, the replacement of iodine by the methylthio functionality is expected to result in the presentation of a comparable steric surface on the aromatic ring.
    • (1956) J. Am. Chem. Soc. , vol.78 , pp. 5920-5923
    • Mislow, K.1    Meluch, W.C.2
  • 31
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    • and references therein
    • Iodine and the ethyl group have similar values in Taft's steric scale (see: March, J. Advanced Organic Chemistry; John Wiley and Sons: New York, 1992; p 285, and references therein). Sulfur is isosteric with methylene. For example, see Mislow's determination of the absolute configuration of α-lipoic acid (Mislow, K. and Meluch, W. C. J. Am. Chem. Soc. 1956, 78, 5920-5923) and the formation of similar polymorphic crystal forms of D,L-methionine and D,L-norleucine (see Dalhus, B. and Gorbitz, C. H. Acta Crystallogr., Sect. C (Cs. Str. Comm.) 1999, 55, 1105-1112, and references therein). Therefore, the replacement of iodine by the methylthio functionality is expected to result in the presentation of a comparable steric surface on the aromatic ring.
    • (1999) Acta Crystallogr., Sect. c (Cs. Str. Comm.) , vol.55 , pp. 1105-1112
    • Dalhus, B.1    Gorbitz, H.C.2
  • 32
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    • note
    • The dipolar interaction between the exocyclic nitrogen of guanine and the iodine should be significantly stronger than that between the external methyl group of the methylthio functionality and the guanine amino group. The internal sulfur atom is not expected to contact the DNA due to steric hindrance from the external methyl group and the two ortho-functionalities on the aromatic ring (see Figure 1).
  • 38
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    • Ph.D. Thesis, Princeton University
    • Pal, S. Ph.D. Thesis, Princeton University, 1997.
    • (1997)
    • Pal, S.1
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    • Scatchard, G. Ann. N. Y. Acad. Sci. 1949, 51, 600-604. The relative linearity of the data from the binding isotherm, representing the formation of a 1:1 complex, validates the use of a simple Scatchard analysis, rather than a neighbor exclusion model (McGhee, J. D.; von Hippel, P. H. J. Mol. Biol. 1974, 86, 469-489). We thank a reviewer for this observation.
    • (1949) Ann. N. Y. Acad. Sci. , vol.51 , pp. 600-604
    • Scatchard, G.1
  • 46
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    • Scatchard, G. Ann. N. Y. Acad. Sci. 1949, 51, 600-604. The relative linearity of the data from the binding isotherm, representing the formation of a 1:1 complex, validates the use of a simple Scatchard analysis, rather than a neighbor exclusion model (McGhee, J. D.; von Hippel, P. H. J. Mol. Biol. 1974, 86, 469-489). We thank a reviewer for this observation.
    • (1974) J. Mol. Biol. , vol.86 , pp. 469-489
    • McGhee, J.D.1    Von Hippel, P.H.2
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    • a's at 298 K
    • a's at 298 K.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.