Tyrosine sulfation

Farzan M, Mirzabekov T, Kolchinsky P, Wyatt R, Cayabyab M, Gerard NP, Gerard C, Sodroski J, Choe H (1999) Tyrosine sulfation of the amino terminus of CCR5 fadlitates HlV-1 entry. Cell 96 667-676... 

Fong AM, Alam SM, hnai T, Haribabu B, Patel DD. CX3CR1 tyrosine sulfation enhances fractalkine-induced cell adhesion. J Biol Chem 2002 277 19418-23. 

Preobrazhensky AA, Dragan S, Kawano T, et al. Monocyte chemotactic protein-1 receptor CCR2B is a glycoprotein that has tyrosine sulfation in a conserved extracellular N-terminal region. J Immunol 2000 165 5295-303. 

Seibert C, Cadene M, Sanhz A, Chait BT, Sakmar TP. Tyrosine sulfation of CCR5 N-terminal peptide by tyrosylprotein sulfotransferases 1 and 2 follows a discrete pattern and temporal sequence. Proc Natl Acad Sci U S A 2002 99(17) 11031— 11036. 

The most potent thrombin inhibitor is hirudin, originally isolated from the salivary glands of the medicinal leech Hirudo medicinalis. Its inhibition constant is in the femtomolar (10-15 M) range (57). It is a 65-amino-acid tyrosine-sulfated single-chain polypeptide. Recombinant hirudin differs from native hirudin by the absence of the sulfate group on tyrosine 63 (Tyr-63) and is referred to as desulfato hirudin. The loss of this sulfate group reduces the thrombin inhibitory potency by 10-fold. 

M Bodanszky, J Martinez, GP Priestly, JD Gardner, V Mutt. Synthesis and properties of a biologically active analog of the C-terminal heptapeptide with e-hydroxy-norleucine sulfate replacing tyrosine sulfate. J Med Chem 21 1030-1037, 1978. 

Farzan M, Vasilieva N, Schnitzler CE et al (2000) A tyrosine-sulfated peptide based on the N-terminus of CCR5 interacts with a CD4-enhanced epitope of the HIV-1 gpl20 envelope glycoprotein and inhibits HIV-1 entry. J Biol Chem 275 33516-33521... 

Huang CC, Lam SN, Acharya P et al (2007) Structures of the CCR5 N terminus and of a tyrosine-sulfated antibody with HIV-1 gpl20 and CD4. Science 317 1930-1934... 

Acharya P, Dogo-Isonagie C, Lalonde JM et al (2011) Structure-based identification and neutralization mechanism of tyrosine sulfate mimetics that inhibit HIV-1 entry. ACS Chem Biol 6 1069-1077... 

Spectral alterations of the tyrosyl spectrum resulting from the formation of an ether linkage with the phenolic oxygen may be quite small, as with 0-methyltyrosine (Wetlaufer et al. 1958), or substantial, as with the aromatic ether thyronine (Gemmill, 1955). The ester linkage is also of some interest in this connection, since tyrosine-O-sulfate has been shown by Bettelheim (1954) to occur in bovine fibrinogen. The spectrum of tyrosine sulfate .. . differs markedly from that of tyrosine, showing a much weaker absorption with a maximum near 2630 A. ... 

Koeller KM, Smith MEB, Huang RE, Wong CH Chemoenzy-matic synthesis of a PSGL-1 A-terminal glycopeptide containing tyrosine sulfate and alpha-O-linked sialyl Lewis X. J. Am. Chem. Soc. 2000 122 4241-4242. 

Leppanen A, White SP, Helin J, McEver RP, Cummings RD. Binding of glycosulfopeptides to P-selectin requires stereospecific contributions of individual tyrosine sulfate and sugar residues. J. Biol. Chem. 2000 275 39569-39578. 

Dong J-F, Li CQ, Lopez JA Tyrosine sulfation of the glycoprotein Ib-IX complex Identificaticm of sulfated residues and ect cm ligand binding. Biodiemisiry 33 13946,1994... 

Sakakibara, V., Katafuchi. J., Takami. Y, Nakayama, T, Suifco, M., Nakajima, H., and Liu, M.-C. (1997). Mangancse-depwient DOPA/tyrosine sulfation in HepG2 human hepatoma cells. Btticffpm. Biophyi. Acts 1335, 102-106. 

Huttner, W. B. (1907). Protein tyrosine sulfation. Twids Biol- Sci. 12,361-363-... 

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