Kovacik V, Patoprsty V, Lattova E, Petrus L, Ovcharenko V, Pihlaja K
Institute of Chemistry, Slovak Academy of Sciences, Dubravska cesta 9, SK-84238 Bratislava, Slovak Republic.
J Mass Spectrom. 1999 Dec;34(12):1322-7. doi: 10.1002/(SICI)1096-9888(199912)34:12<1322::AID-JMS888>3.0.CO;2-#.
O-Isopropylidene and O-benzylidene acetals of common 2, 6-anhydro-1-deoxy-1-nitroalditols (beta-D-glyco- pyranosylnitromethanes) derived from D-glucose, D-galactose and D-mannose were studied by electron ionization (EI) mass spectrometry. Fragment pathways of the title compounds were studied using accurate mass measurements, collision-induced dissociation, B/E and B2/E measurements of selected ions and mass spectra of O-deuterium-labelled compound. The fragmentation pathways and some differences found among the mass spectra of stereoisomers are discussed. Noteworthy is the splitting off of the (.)NO(2) radical and elimination of acetone from the molecular ions of 4, 6-O-benzylidene-2, 3-O-isopropylidene-beta-D-galactopyranosylnitromethane. This fragmentation route of relatively high abundance was not observed in the case of D-gluco and D-manno analogues. The differences in the EI mass spectra of stereoisomers may help to provide some information serving for the estimation of the stereochemical arrangement of compounds of this type. Copyright 1999 John Wiley & Sons, Ltd.
采用电子电离（EI）质谱法对由D-葡萄糖、D-半乳糖和D-甘露糖衍生的常见2,6-脱水-1-脱氧-1-硝基糖醇（β-D-吡喃糖基硝基甲烷）的O-异亚丙基和O-亚苄基缩醛进行了研究。利用精确质量测量、碰撞诱导解离、选定离子的B/E和B2/E测量以及O-氘代标记化合物的质谱，研究了标题化合物的碎裂途径。讨论了立体异构体质谱中的碎裂途径及一些差异。值得注意的是，4,6-O-亚苄基-2,3-O-异亚丙基-β-D-吡喃半乳糖基硝基甲烷的分子离子会脱去（·）NO(2)自由基并消除丙酮。在D-葡萄糖和D-甘露糖类似物的情况下未观察到这种丰度相对较高的碎裂途径。立体异构体EI质谱的差异可能有助于提供一些信息，用于估算此类化合物的立体化学排列。版权所有1999约翰威立父子有限公司。
