Glycophosphoceramides from plants. Purification and characterization of a novel tetrasaccharide derived from tobacco leaf glycolipids.
Glycophosphoceramides from plants. Purification and characterization of a novel tetrasaccharide derived from tobacco leaf glycolipids.
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来自植物的糖基磷酸神经酰胺。
DOI：
10.1016/s0021-9258(18)43340-6
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发表时间：
1981
期刊：
影响因子：
--
通讯作者：
R. Laine
中科院分区：
文献类型：
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作者：
T. C. Hsieh;R. Lester;R. Laine
从烟叶中制备的糖磷神经酰胺浓缩物被证明含有相关脂质的混合物(Kaul， K., and Lester， R. L. (1975) Plant Physiol. 55, 120-129；Kaul， K., and Lester， R. L.（1978）生物化学17,3569-3575)与最简单和最丰富的结构成分GlcN(+/- Ac)(α 1导致4)GlcUA（α 1导致2）肌醇-1- o -磷酸化神经酰胺（Hsieh， T. C.-Y.）。， Kaul， K., Laine， R. A.和Lester， R. L.（1978）生物化学17,3575-3579)。为了确定该系列中更复杂的成员的结构，通过碱催化水解和碱性磷酸酶处理，将羧基还原的糖磷神经酰胺浓缩物制备了低聚糖混合物。反相高压液相色谱的组合（Wells, g.b.和Lester， r.l., 1979）。采用正相高压液相色谱法和薄层色谱法对几种低聚糖的乙酰化衍生物进行了分离。甲基化分析、CrO3氧化和脱乙酰脱胺的产物使用化学电离质谱法进行了鉴定，得到了以下新的结构。一个主要的四糖被完全表征为Gal(α 1导致4)GlcNAc(α 1导致4)GlcUA（α 1导致2）肌醇。一种次要四糖的附加结构被部分表征为GlcNAc(α 1导致4)GlcUA（α 1导致？）肌醇（O从1 α导致）Man。这些是植物中一类酸性糖脂的代表，可能类似于动物细胞膜中发现的酸性神经节苷。
A glycophosphoceramide concentrate prepared from tobacco leaves was shown to contain a mixture of related lipids (Kaul, K., and Lester, R. L. (1975) Plant Physiol. 55, 120-129; Kaul, K., and Lester, R. L. (1978) Biochemistry 17, 3569-3575) with the simplest and most abundant components having the structure GlcN(+/- Ac)(alpha 1 leads to 4)GlcUA(alpha 1 leads to 2)myoinositol-1-O-phosphorylceramide (Hsieh, T. C.-Y., Kaul, K., Laine, R. A., and Lester, R. L. (1978) Biochemistry 17, 3575-3579). To determine the structure of the more complex members of this series, a mixture of oligosaccharides was prepared from a carboxyl-reduced glycophosphoceramide concentrate by alkali-catalyzed hydrolysis and alkaline phosphatase treatment. A combination of reverse-phase high pressure liquid chromatography (Wells, G. B., and Lester, R. L. (1979) Anal. Biochem. 97, 184-190), normal-phase high pressure liquid chromatography, and thin layer chromatography were used to resolve several oligosaccharides as acetylated derivatives. Products of methylation analysis, CrO3 oxidation, and deacetylation-deamination were identified using chemical ionization mass spectrometry to give the following novel structures. A major tetrasaccharide was completely characterized as Gal(alpha 1 leads to 4)GlcNAc(alpha 1 leads to 4)GlcUA(alpha 1 leads to 2)myoinositol. An additional structure of a minor tetrasaccharide was partially characterized as GlcNAc(alpha 1 leads to 4)GlcUA(alpha 1 leads to ?)myoinositol(O leads from 1 alpha)Man. These are representatives of a class of acidic glycolipids from plants, possibly analogous to the acidic gangliosides found in animal cell membranes.