Gusakova V, Denisov G S, Kagan E Z
Antibiot Khimioter. 1988 Sep;33(9):657-60.
IR spectra (1600-1800 and 3000-3650 cm-1) of lincomycin base solutions in inert (CCl4 and C2Cl4), proton acceptor (dioxane, dimethylsulfoxide and triethyl amine) and proton donor (CHCl3, CD3OD and D2O) solvents were studied. Analysis of the concentration and temperature changes in the spectra revealed that association in lincomycin in the inert solvents was due to intramolecular hydrogen linkage involving amide and hydroxyl groups. Disintegration of the associates after the solution dilution and temperature rise was accompanied by formation of intramolecular bonds stabilizing the stable conformation structure of the lincomycin molecule. The following hydrogen linkage in the conformation was realized: NH...N (band v NH...N at 3340 cm-1), OH...O involving the hydroxyl at C-7 and O atoms in the D-galactose ring (band v OH...O at 3548 cm-1), a chain of the hydrogen bonds OH...OH...OH in the lincomycin carbohydrate moiety (band v OH...O at 3593 cm-1 and v OH of the end hydroxyl group at 3625 cm-1). Bonds NH and C-O of the amide group were located in transconformation. Group C-O did not participate in the intramolecular hydrogen linkage.
研究了林可霉素碱溶液在惰性溶剂（四氯化碳和四氯乙烯）、质子受体（二氧六环、二甲基亚砜和三乙胺）和质子供体（氯仿、氘代甲醇和重水）中的红外光谱（1600 - 1800和3000 - 3650 cm⁻¹）。光谱中浓度和温度变化的分析表明，在惰性溶剂中林可霉素的缔合是由于涉及酰胺和羟基的分子内氢键。溶液稀释和温度升高后缔合体的分解伴随着分子内键的形成，这些键稳定了林可霉素分子的稳定构象结构。构象中的以下氢键得以实现：NH...N（在3340 cm⁻¹处有v NH...N谱带）、OH...O涉及C - 7位的羟基和D - 半乳糖环中的O原子（在3548 cm⁻¹处有v OH...O谱带）、林可霉素碳水化合物部分中OH...OH...OH氢键链（在3593 cm⁻¹处有v OH...O谱带和末端羟基的v OH在3625 cm⁻¹处）。酰胺基团的NH和C - O键处于反式构象。C - O基团不参与分子内氢键。
