Structural determination of novel lacto-N-decaose and its monofucosylated analogue from human milk by electrospray tandem mass spectrometry and 1H NMR spectroscopy

被引:38
作者
Chai, WG
Piskarev, VE
Zhang, YB
Lawson, AM
Kogelberg, H
机构
[1] Imperial Coll Fac Med, MRC Glycosci Lab, Harrow HA1 3UJ, Middx, England
[2] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 117813, Russia
基金
英国医学研究理事会;
关键词
electrospray mass spectrometry; tandem mass spectrometry; NMR human milk; oligosaccharide; lacto-N-decaose; Lewis antigen;
D O I
10.1016/j.abb.2004.09.035
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
We have isolated and characterised two neutral oligosaccharides, one nonfucosylated and the other monofucosylated, from human milk that are based on the doubly branched lacto-N-decaose core. Their structures have been determined by a combined use of electrospray tandem mass spectrometry (ES-MS/MS) and NMR spectroscopy. The sequences of the three branches resulted from the double-branching, including the identity and location of the blood-group-related Lewis determinant and partial linkages, were elucidated by the unique method of high sensitivity negative-ion ES-MS/MS analysis. Their full Structure assignment was completed by methylation analysis and H-1 NMR. The monofucosylated lacto-N-decaose, Galbeta1-4(Fucalpha1-3)GlcNAcbeta1-6(Galbeta1-3GlcNAcbeta1-3)-Galbeta1-4GlcNAcbeta1-6(Galbeta1-3GlcNAcbeta1-3)Galbeta1-4Glc is a novel sequence, whereas the nonfucosylated lacto-N-decaose, Galbeta1-4GlcNAcbeta1-6(Galbeta1-3GlcNAcbeta1-3)Galbeta1-4GlcNAcbeta1-6(Galbeta1-3GlcNAcbeta1-3)Galbeta1-4Glc, has not been isolated and identified as an individual oligosaccharide. (C) 2004 Elsevier Inc. All rights reserved.
引用
收藏
页码:116 / 127
页数:12
相关论文
共 24 条
[1]   FUCOSE-CONTAINING OLIGOSACCHARIDES FROM HUMAN-MILK FROM A DONOR OF BLOOD GROUP-0 LEA NONSECRETOR [J].
BRUNTZ, R ;
DABROWSKI, U ;
DABROWSKI, J ;
EBERSOLD, A ;
PETERKATALINIC, J ;
EGGE, H .
BIOLOGICAL CHEMISTRY HOPPE-SEYLER, 1988, 369 (04) :257-273
[2]   Nonreductive release of O-linked oligosaccharides from mucin glycoproteins for structure/function assignments as neoglycolipids: application in the detection of novel ligands for E-selectin [J].
Chai, WG ;
Feizi, T ;
Yuen, CT ;
Lawson, AM .
GLYCOBIOLOGY, 1997, 7 (06) :861-872
[3]   NEUTRAL OLIGOSACCHARIDES OF BOVINE SUBMAXILLARY MUCIN - A COMBINED MASS-SPECTROMETRY AND H-1-NMR STUDY [J].
CHAI, WG ;
HOUNSELL, EF ;
CASHMORE, GC ;
ROSANKIEWICZ, JR ;
BAUER, CJ ;
FEENEY, J ;
FEIZI, T ;
LAWSON, AM .
EUROPEAN JOURNAL OF BIOCHEMISTRY, 1992, 203 (1-2) :257-268
[4]   Branching pattern and sequence analysis of underivatized oligosaccharides by combined MS/MS of singly and doubly charged molecular ions in negative-ion electrospray mass spectrometry [J].
Chai, WG ;
Piskarev, V ;
Lawson, AM .
JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY, 2002, 13 (06) :670-679
[5]   Negative ion electrospray mass spectrometry of neutral underivatized oligosaccharides [J].
Chai, WG ;
Piskarev, V ;
Lawson, AM .
ANALYTICAL CHEMISTRY, 2001, 73 (03) :651-657
[6]   LIGAND RECOGNITION BY E-SELECTIN - SYNTHESIS, INHIBITORY ACTIVITY, AND CONFORMATIONAL-ANALYSIS OF BIVALENT SIALYL-LEWIS-X ANALOGS [J].
DEFREES, SA ;
KOSCH, W ;
WAY, W ;
PAULSON, JC ;
SABESAN, S ;
HALCOMB, RL ;
HUANG, DH ;
ICHIKAWA, Y ;
WONG, CH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (01) :66-79
[7]   A SYSTEMATIC NOMENCLATURE FOR CARBOHYDRATE FRAGMENTATIONS IN FAB-MS MS SPECTRA OF GLYCOCONJUGATES [J].
DOMON, B ;
COSTELLO, CE .
GLYCOCONJUGATE JOURNAL, 1988, 5 (04) :397-409
[8]   Carbohydrate-mediated recognition systems in innate immunity [J].
Feizi, T .
IMMUNOLOGICAL REVIEWS, 2000, 173 :79-88
[10]   PRIMARY STRUCTURE OF HUMAN-MILK OCTASACCHARIDES, DODECASACCHARIDES AND TRIDECASACCHARIDES DETERMINED BY A COMBINATION OF H-1-NMR SPECTROSCOPY AND FAST-ATOM-BOMBARDMENT MASS-SPECTROMETRY - EVIDENCE FOR A NEW CORE STRUCTURE, THE PARA-LACTO-N-OCTAOSE [J].
HAEUWFIEVRE, S ;
WIERUSZESKI, JM ;
PLANCKE, Y ;
MICHALSKI, JC ;
MONTREUIL, J ;
STRECKER, G .
EUROPEAN JOURNAL OF BIOCHEMISTRY, 1993, 215 (02) :361-371