Abstract

Ansamycins are a very specific class of macrocyclic antibiotics of which the rifamycins are among the better-known members. Rifamycins bind to and inhibit DNA polymerase. Rifamycin B (the most easily obtained ansamycin) is negatively charged and is shown to associate with and enantioselectively resolve several chiral amino alcohols including terbutaline, isoproterenol, bamethan, metaproterenoi, synephrine, metanephrine, salbutamol, epinephrine, norphenylephrine, ephedrine, ψ-ephedrine, octopamine, norepinephrine, normetanephrine, metoprolol, alprenolol, atenolol, and oxprenolol. A description of the structure and properties of rifamycins, in general, and rifamycin B, in particular, is given. The complexation and chiral recognition of the aforementioned racemic compounds by rifamycin B is afforded by multiple interactions of which charge-charge, hydrogen-bonding, and hydrophobic inclusion interactions most likely dominate in hydroorganic solvents. The effect of various experimental factors on enantiomeric resolution is discussed in terms of optimizing the CE separations. Since most chiral antibiotic macrocycles are ionizable, somewhat flexible, and contain hydrophobic and hydrophilic moieties, they tend to be significantly affected by variations in the solution environment. © 1994, American Chemical Society. All rights reserved.

Department(s)

Chemistry

Comments

National Institute of General Medical Sciences, Grant R01GM036292

International Standard Serial Number (ISSN)

1520-6882; 0003-2700

Document Type

Article - Journal

Document Version

Citation

File Type

text

Language(s)

English

Rights

© 2024 American Chemical Society, All rights reserved.

Publication Date

01 May 1994

PubMed ID

8030783

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