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Chemical Compound Review:

Nag-4-S (2R,3S,4R,5R)-5-acetamido- 1,2,4-trihydroxy...

Synonyms: AC1L566Z, 45233-43-0

Tsuji, M. et al., Ohtake, S. et al., Jackson, C.E. et al., Kodama, C. et al., Balbaa, M. et al., et al.

Balbaa, Bassiouny,

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Disease relevance of N-Acetylgalactosamine 4-sulfate

A sample from a patient with Maroteaux-Lamy syndrome showed peaks for N-acetylgalactosamine-4-sulfate and the disaccharide-4-sulfate, but neither peak x nor peak y [1].

High impact information on N-Acetylgalactosamine 4-sulfate

Leukocytes, urine, and cultured skin fibroblasts revealed a deficiency of arylsulfatase B (N-acetylgalactosamine 4-sulfate sulfatase) [2].
N-Acetylgalactosamine 4-sulfate 6-O-sulfotransferase (GalNAc4S-6ST) transfers sulfate from 3'-phosphoadenosine 5'-phosphosulfate to position 6 of N-acetylgalactosamine 4-sulfate (GalNAc(4SO(4))) in chondroitin sulfate and dermatan sulfate [3].
Arylsulfatase B (ASB) hydrolyzes the desulfation of N-acetylgalactosamine-4-sulfate at the non-reducing terminal of glycosaminoglycans [4].
Using chondroitin [35S]sulfate from chick embryo cartilage, it is shown that hydrolysis of ester sulfate by this enzyme is limited to 4-sulfate groups occurring in the non-reducing terminal N-acetylgalactosamine 4-sulfate and N-acetylgalactosamine 4,6-bissulfate residues [5].

Biological context of N-Acetylgalactosamine 4-sulfate

Arylsulfatase B (ARSB) is the lysosomal enzyme that catalyzes the hydrolysis of 4-sulfate groups from N-acetylgalactosamine 4-sulfate moieties on the glycosaminoglycans, dermatan sulfate and chondroitin sulfate A [6].

References

Liquid-chromatographic determination of urinary glycosaminoglycans for differential diagnosis of genetic mucopolysaccharidoses. Kodama, C., Ototani, N., Isemura, M., Aikawa, J., Yosizawa, Z. Clin. Chem. (1986) [Pubmed]
Deficiency of arylsulfatase B in 2 brothers aged 40 and 38 years (Maroteaux-Lamy syndrome, type B). Pilz, H., von Figura, K., Goebel, H.H. Ann. Neurol. (1979) [Pubmed]
Human N-acetylgalactosamine 4-sulfate 6-O-sulfotransferase cDNA is related to human B cell recombination activating gene-associated gene. Ohtake, S., Ito, Y., Fukuta, M., Habuchi, O. J. Biol. Chem. (2001) [Pubmed]
In vitro effect of schistosomicidal drugs on hepatic arylsulfatase B from the schistosoma-infected mouse. Balbaa, M., Bassiouny, K. Journal of enzyme inhibition and medicinal chemistry. (2006) [Pubmed]
The common identity of UDP-N-acetylgalactosamine 4-sulfatase, nitrocatechol sulfatase (arylsulfatase), and chondroitin 4-sulfatase. Tsuji, M., Nakanishi, Y., Habuchi, H., Ishihara, K., Suzuki, S. Biochim. Biophys. Acta (1980) [Pubmed]
Feline arylsulfatase B (ARSB): isolation and expression of the cDNA, comparison with human ARSB, and gene localization to feline chromosome A1. Jackson, C.E., Yuhki, N., Desnick, R.J., Haskins, M.E., O'Brien, S.J., Schuchman, E.H. Genomics (1992) [Pubmed]

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