TY - JOUR
T1 - Crystal structure, conformation, and absolute configuration of kanamycin A
AU - Puius, Yoram A.
AU - Stievater, Todd H.
AU - Srikrishnan, Thamarapu
N1 - Funding Information:
Our thanks are due to the National Science Foundation for the award of a fellowship to Yoram Puius and Todd Stievater.
PY - 2006/12/11
Y1 - 2006/12/11
N2 - Kanamycin, an antibiotic complex produced by Streptomyces kanamycetius isolated from Japanese soil, was described by Okami and Umezawa as early as 1957 and consists of three components: Kanamycin A (the major component), B, and C. The disulfate salt of kanamycin A [4-O-(6-amino-6-deoxy-α-d-glucopyranosyl)-6-O-(3-amino-3-deoxy-α-d-glucopyranosyl)-2-deoxystreptamine] is a broad-spectrum antibiotic that is used to treat gonorrhea, salmonella, tuberculosis, and many other diseases. Crystals of kanamycin A monosulfate monohydrate obtained from water are triclinic, space group P1, with a = 7.2294(14), b = 12.4922(15), c = 7.1168(9), α = 94.74(1), β = 89.16(1), γ = 91.59(1), V = 640.2(2) Å3, μ(Cu Kα) = 18.4 cm-1, FW 600.6, Dcalc = 1.558 g/cm3, CAD-4 diffractometric data (2693 reflections, 2554 ≥ 3σ(I)), structure by shelx-86 and refined by full-matrix least squares to a final R value of 0.038. The wrong conformer had an R value of 0.043. Both of the d-glucose moieties are attached to the deoxystreptamine by α linkages. This absolute configuration agrees with the earlier determination by both chemical and X-ray methods with photographic data. The (φ{symbol}, ψ) values for the glycosidic linkages are 101.6°, -121.1°, 106.3°, and -140.4°, respectively. Kanamycin interacts with the ribosomal S12 protein to stabilize the codon-anticodon binding between mRNA and the aminoacyl tRNA and inhibits the elongation of peptide chains through a series of reactions resulting in the prevention of ribosomes from moving along mRNA.{A figure is presented}.
AB - Kanamycin, an antibiotic complex produced by Streptomyces kanamycetius isolated from Japanese soil, was described by Okami and Umezawa as early as 1957 and consists of three components: Kanamycin A (the major component), B, and C. The disulfate salt of kanamycin A [4-O-(6-amino-6-deoxy-α-d-glucopyranosyl)-6-O-(3-amino-3-deoxy-α-d-glucopyranosyl)-2-deoxystreptamine] is a broad-spectrum antibiotic that is used to treat gonorrhea, salmonella, tuberculosis, and many other diseases. Crystals of kanamycin A monosulfate monohydrate obtained from water are triclinic, space group P1, with a = 7.2294(14), b = 12.4922(15), c = 7.1168(9), α = 94.74(1), β = 89.16(1), γ = 91.59(1), V = 640.2(2) Å3, μ(Cu Kα) = 18.4 cm-1, FW 600.6, Dcalc = 1.558 g/cm3, CAD-4 diffractometric data (2693 reflections, 2554 ≥ 3σ(I)), structure by shelx-86 and refined by full-matrix least squares to a final R value of 0.038. The wrong conformer had an R value of 0.043. Both of the d-glucose moieties are attached to the deoxystreptamine by α linkages. This absolute configuration agrees with the earlier determination by both chemical and X-ray methods with photographic data. The (φ{symbol}, ψ) values for the glycosidic linkages are 101.6°, -121.1°, 106.3°, and -140.4°, respectively. Kanamycin interacts with the ribosomal S12 protein to stabilize the codon-anticodon binding between mRNA and the aminoacyl tRNA and inhibits the elongation of peptide chains through a series of reactions resulting in the prevention of ribosomes from moving along mRNA.{A figure is presented}.
KW - Absolute configuration
KW - Crystal structure
KW - Kanamycin A
KW - Stereochemistry
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U2 - 10.1016/j.carres.2006.09.008
DO - 10.1016/j.carres.2006.09.008
M3 - Article
C2 - 17052696
AN - SCOPUS:33750604952
SN - 0008-6215
VL - 341
SP - 2871
EP - 2875
JO - Carbohydrate Research
JF - Carbohydrate Research
IS - 17
ER -
