Synthesis of phosphorylated pentasaccharides found on asparagine-linked carbohydrate chains of lysosomal enzymes

1987 ◽  
Vol 52 (13) ◽  
pp. 2869-2875 ◽  
Author(s):  
Om P. Srivastava ◽  
Ole Hindsgaul
1986 ◽  
Vol 64 (12) ◽  
pp. 2324-2330 ◽  
Author(s):  
Om. P. Srivastava ◽  
Ole Hindsgaul

The three possible subterminally 6-O-phosphorylated trimannosides (2–4) found on the asparagine-linked carbohydrate chains of lysosomal enzymes have been chemically synthesized as their 8-methoxycarbonyloctyl glycosides, R = (CH2)8COOCH3. The key step in the syntheses involves glycosylation of suitably protected α-D-mannopyranosides 5–7 with the phosphorylated mannobiosyl donor 2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-3,4-di-O-benzyl-6-O-di-phenylphosphoryl-α-D-mannopyranosyl chloride (14), which produced mixtures of α- and β-linked trisaccharidic products. Compounds 2 (αDMan(1 → 2) αDMan 6-phosphate(1 → 2)αDManOR), 3 (αDMan(1 → 2)αDMan 6-phosphate(1 → 3)αDManOR), and 4 (αDMan(1 → 2)αDMan 6-phosphate(1 → 6)αDManOR) are being used in a study of the targeting of enzymes to the lysosomes by phosphomannosyl receptors.


2002 ◽  
Vol 2 (5) ◽  
pp. 423-437 ◽  
Author(s):  
Sandra Hofmann ◽  
Armita Atashband ◽  
Steve Cho ◽  
Amit Das ◽  
Praveena Gupta ◽  
...  

1969 ◽  
Vol 27 (2-4) ◽  
pp. 115-127 ◽  
Author(s):  
H. D. Bartsch ◽  
K. -O. Habermehl ◽  
W. Diefenthal

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