Crystal and molecular structure and absolute configuration of lincomycin hydrochloride monohydrate

[Display omitted] Lincomycin is a broad-spectrum antibiotic synthesized by Streptomyces lincolnensis that is particularly active against Gram-positive bacteria. It is widely used in human and veterinary applications. The crystal structure of lincomycin has been undertaken with a view to obtain the c...

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Bibliographic Details
Published in:Carbohydrate research 2004-08, Vol.339 (12), p.2111-2115
Main Authors: Rajeswaran, Manju, Srikrishnan, Thamarapu
Format: Article
Language:English
Subjects:
Absolute configuration
Crystal structure
Crystallization
Crystallography, X-Ray
Hydrogen Bonding
Lincomycin
Lincomycin - chemistry
Models, Molecular
Molecular Structure
Stereochemistry
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Summary:[Display omitted] Lincomycin is a broad-spectrum antibiotic synthesized by Streptomyces lincolnensis that is particularly active against Gram-positive bacteria. It is widely used in human and veterinary applications. The crystal structure of lincomycin has been undertaken with a view to obtain the conformational and structural features of the drug in order to afford a comparison of its structural features with other aminoglycoside antibiotics. We report here the details of its structural and conformational features as determined by single-crystal X-ray crystallography. Crystals of lincomycin hydrochloride are orthorhombic, space group P2 1 2 1 2, with the cell dimensions a = 18.5294(3) Å, b = 20.5980(4) Å, c = 6.17380(10) Å, V = 2356.35(7) Å 3. The structure was solved using X-ray diffraction data and refined to a final R-value of 0.0391 for 2321 reflections ( I ⩾ 2 σ). The absolute configuration was established using the anomalous dispersion of the sulfur and chlorine atoms in the structure. The molecule consists of an amino acid linked by an amide group to a monosaccharide of galactose stereochemistry. A network of hydrogen-bonds stabilizes the crystal structure.
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2004.05.032