Iwanowitsch A, Friebolin H, Carganico R, Errenst M, Weisshaar G, Brunner H, Mann H
Organisch-Chemisches Institut, Universität Heidelberg, Germany.
Biol Chem. 1998 Jun;379(6):737-41.
Five oligosaccharide alpha1-phosphates and one sulfated glycopeptide have been isolated from the hemofiltrate of one patient with end-stage renal disease. Isolation of these compounds has been achieved using reverse osmosis, ion-exchange and size-exclusion chromatography and high performance liquid chromatography. The structures were predominantly elucidated by one- and two-dimensional 1H and 31P NMR spectroscopy. The chemical structures were determined to be: 1 NeuAc alpha2-3Gal alpha1-OPO3H2; 2 NeuAc alpha2-6Galbeta1-4GlcNAc alpha1-OPO3H2; 3 NeuAc alpha2-3Galbeta1-3GalNAc alpha1-OPO3H2; 4 NeuAc alpha2-3Galbeta1-3[NeuAc alpha2-6]GalNAc alpha1-OPO3H2 (proposed structure); 5 Fuc alpha1-2Galbeta1-4[Fuc alpha1-3]GlcNAc alpha1-OPO3H2; 6 HOSO3-4Fuc alpha1-6GlcNAcbeta1-NAsn. While 2 and 3 have been previously characterized as compounds of urine and hemofiltrate, the oligosaccharide alpha1-phosphates 1, 4, and 5 could be isolated--to our knowledge--for the first time from biological material. Compound 6 is the first glycopeptide reported to contain a 4-sulfated fucose residue.
从一名终末期肾病患者的血液滤过液中分离出了五种低聚糖α1-磷酸酯和一种硫酸化糖肽。这些化合物的分离是通过反渗透、离子交换、尺寸排阻色谱和高效液相色谱实现的。其结构主要通过一维和二维1H和31P NMR光谱进行解析。确定的化学结构如下：1. NeuAcα2-3Galα1-OPO3H2；2. NeuAcα2-6Galβ1-4GlcNAcα1-OPO3H2；3. NeuAcα2-3Galβ1-3GalNAcα1-OPO3H2；4. NeuAcα2-3Galβ1-3[NeuAcα2-6]GalNAcα1-OPO3H2（推测结构）；5. Fucα1-2Galβ1-4[Fucα1-3]GlcNAcα1-OPO3H2；6. HOSO3-4Fucα1-6GlcNAcβ1-NAsn。虽然2和3之前已被鉴定为尿液和血液滤过液中的化合物，但据我们所知，低聚糖α1-磷酸酯1、4和5是首次从生物材料中分离得到的。化合物6是首个报道含有4-硫酸化岩藻糖残基的糖肽。
