Mass spectrometry in structural analysis of natural

J. Lonngren and S. Svensson, Mass spectrometry in structural analysis of natural carbohydrates, Adv. Carbohydr. Chem. Biochem., 29 (1974) 41-106. 

MASS SPECTROMETRY IN STRUCTURAL ANALYSIS OF NATURAL CARBOHYDRATES ... 

Lindberg, B. See Bouveng, H. O. Lonngren, Jorgen, and Svensson, SiGFRiD, Mass Spectrometry in Structural Analysis of Natural Carbohydrates, 29, 41-106 Lohmar, Rolland, and Goepp,... 

Natural carbohydrates, mass spectrometry in structural analysis of, 29, 41—106 Neighboring-group participation, in sugars, 22, 109-175... 

Practical applications are again stressed in the Chapter by Lonngren and Svensson (Stockholm) on Mass Spectrometry in Stmctural Analysis of Natural Carbohydrates. They build on the fundamentals of carbohydrate mass spectrometry, as laid down by Kochetkov and Chizhov in Volume 21, and demonstrate the profound analytical value of mass spectrometry for structural analysis of complex polysaccharides. In particular, this tool has dramatically increased the scope of the traditional methylation linkage-analysis procedure, especially when used in conjunction with gas-liquid chromatographic methods of separation. The latter topic is the subject of complementary Chapters by Dutton, one already published in Volume 28 and the other scheduled for publication in Volume 30. 

Mass spectrometry (m.s.) has become an important and versatile technique in carbohydrate chemistry, and has been reviewed earlier. - The present article deals with m.s. as a tool in the structural analysis of naturally occurring carbohydrates. The mass spectrometry of nucleosides, nucleotides, " sugar phosphates, and related compounds is not included. For natural carbohydrates, studies in which m.s. has only been used for determining molecular weight or elemental composition have also been omitted. 

Great progress in our knowledge about sialic acids was made with the aid of gas-liquid chromatography (g.l.c.), mass spectrometry (m.s.), and n.m.r. spectroscopy. Structural analysis of the many different N- andO-acylated Neu derivatives occurring in Nature will be described in Sections IV,5 and 6. 

In 2002, through the use of nuclear magnetic resonance (NMR) and mass spectrometry/mass spectrometry (MS/MS) analysis, the planar and partial stereostructure of a SAAF from the egg-conditioning medium of C. intestinalis w s elucidated to be a previously uncharacterized sulfated steroid 3,4,7,26-tetrahydroxycholestane-3,26-disulfate (30).73 Its structure was deduced from only 4p.g (6 nmol) of sample. Thus, SAAF may represent the smallest amount of sample used in the structure elucidation of novel nonpeptidic or nonoligosaccharide natural products.74... 

Vilkas and Lederer411 used the procedure for the O- and N-methylation of a natural peptide glycoside and report that it is superior to the Kuhn methylation procedure. Methylation of peptides is useful in the analysis of structures by mass spectrometry. 

Mass spectrometry provides a rapid, sensitive method for the structural analysis of oligosaccharides and, especially in combination with g.l.c., offers a valuable technique for the analysis of oligosaccharides from natural sources and from polysaccharide hydrolyzates. Methyl ethers " or trimethylsilyl ethers are suitable derivatives for the g.l.c. separation of oligosaccharides. 

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