4 Studies on the Synthesis of Sulfur-Containing Glycolipids ("Sulfogylcolipids") ROY GIGG
Downloaded by UNIV OF LEEDS on January 16, 2018 | http://pubs.acs.org Publication Date: June 1, 1978 | doi: 10.1021/bk-1978-0077.ch004
Laboratory of Lipid and General Chemistry, National Institute for Medical Research, Mill Hill, London, NW7 1AA
A sulphur-containing l i p i d was f i r s t detected in brain by Thudichum (1) about one hundred years ago and in 1910 Koch (2) postulated that this l i p i d was a complex between a phospholipid and a sulphated cerebroside. Later Levene (3-5) obtained a sulphur-containing brain l i p i d free from phosphate but it was not until 1933 that Blix (6) obtained a pure sample for which the analytical data indicated that it was a sulphate ester of a cerebroside (1). The presence of the sulphate group on the 3-position of the galactose residue was established in 1962 by Yamakawa (7-8) and Stoffyn (9) by methylation studies and by showing that the compound was stable to periodate oxidation. The β - c o n f i g u r a t i o n of the galactosidic-linkage was established by degradative studies (10) and thus the complete structure (11) of the sulphate ester of cerebroside ("sulphatide") was estab lished. (For reviews see references 11-14). Interest in the sulphatides has increased considerably since the demonstration (15-16) that these compounds accumulate in tissues in the inherited disease known as metachromatic leukodystrophy. This accumulation is due to the deficiency of a sulphatase which normally degrades the sulphatide (11) to a cerebroside (1). In 1963, Martensson (17) isolated a new sulphated l i p i d , from human kidney, which contained both glucose and galactose and this was later (18,19) characterised as the sulphate ester (IV) of the lactosyl ceramide (III). Compound (IV) has also been detected in testicular tissue (20). Another ceramide-contaiηing sulphoglycolipid was detected in hog gastric mucosa in 1974 (2J_) , and this was identified as a triglycosyl ceramide sulphate with the probable structure (VI). The trigly cosyl ceramide (V) is a normal tissue constituent and accumulates in tissues in Fabry's disease due to the deficiency of an α - g a l a c t o s i d a s e . In 1972 a new sulphoglycolipid was reported to be a major component of the glycolipids of mammalian testes and spermatozoa (22-24). This l i p i d ("seminolipid ) differed from the known M
0-8412-0426-8/78/47-077-044$05.75/0 ©
1978 A m e r i c a n C h e m i c a l Society
Schweiger; Carbohydrate Sulfates ACS Symposium Series; American Chemical Society: Washington, DC, 1978.
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