New PDF release: Synthetic Methods of Organic Chemistry

By Theilheimer W.

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Netropsin and distamycin A, which are pyrrole-amidine oligopeptide antibiotics, bind very tightly to A ◊ T regions of Directional Aspects of Intermolecular Interactions 49 a b Fig. 38 a, b. Minor groove binding of netropsin in DNA [100]: a chemical formula of netropsin; b binding of netropsin by way of N-H◊◊ ◊ ◊O bonds (dotted lines) and C-H◊◊ ◊ ◊C interactions. The latter define the specificity of the drug duplex DNA, as illustrated in Fig. 38. These compounds are relatively cytotoxic. In the crystal structure of netropsin bound to a dodecamer with four A ◊ T base pairs in the middle, the four base pairs have high propeller twists [99, 100].

In this compound the amino groups are joined by a xylyl group. This daunomy- a Fig. 37a–c. Binding of daunomycin to an oligonucleotide [95]: a chemical formula of daun- omycin, showing some interactions in the crystalline state. R1 =CH3 , R2 =CH3 for daunomycin, CH2OH for adriamycin Directional Aspects of Intermolecular Interactions 47 b c Fig. 37b, c. P. Glusker d Fig. 37d. The chemical formula of a bisintercalator, WP 631 [97] cin derivative (named WP631, see Fig. 7 ¥ 1011 M–1 for WP631 [98].

This is shown in Fig. 16. Thus there are two important types of interactions involving delocalized p-electron systems, as described earlier. These are the C-H◊◊ ◊ ◊p or C-H◊◊ ◊ ◊C interactions (where p may be any part of an electron-rich aromatic system, a delocalized double bond or a triple carbon-carbon bond) which give rise to a “herring-bone” arrangement of molecules, as shown for benzene in Fig. 2. O-H◊◊ ◊ ◊p interactions are also seen in 2- and 3-aminophenol crystals in 2ethynyladamantan-2-ol [47], and in several protein structures in the PDB.

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Synthetic Methods of Organic Chemistry by Theilheimer W.


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