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Volumn 43, Issue 7, 2004, Pages 828-833

Glyco-SeS: Selenenylsulfide-mediated protein glycoconjugation - A new strategy in post-translational modification

Author keywords

Carbohydrates; Glycoproteins; Glycosylation; Protein modifications; Selenium

Indexed keywords

CARBOHYDRATES; CHEMICAL BONDS; MOLECULAR STRUCTURE; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

EID: 4544387352     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200352975     Document Type: Article
Times cited : (152)

References (48)
  • 1
    • 0034887203 scopus 로고    scopus 로고
    • The Gene Ontology Consortium has defined biological-process term-number GO:0006486 (protein amino acid glycosylation) as "The addition of a sugar unit to a protein amino acid, for example, the addition of glycan chains to protein." (see Genome Res. 2001, 11, 1425). Herein we use the broader term glycoconjugation to refer to the general process of addition of a glycosyl-unit-containing moiety to another moiety through a covalent linkage.
    • (2001) Genome Res. , vol.11 , pp. 1425
  • 8
    • 0035937424 scopus 로고    scopus 로고
    • J. B. Lowe, Cell 2001, 104, 809.
    • (2001) Cell , vol.104 , pp. 809
    • Lowe, J.B.1
  • 11
    • 0000962459 scopus 로고    scopus 로고
    • The recent preparation of homogeneous W-glycosylated protein in yeast represents a remarkable ac hievement in this regard; see: S. R. Hamilton, P. Bobrowicz, B. Bobrowicz, R. C. Davidson, H. Li, T. Mitchell, J. H. Nett, S. Rausch, T. A. Stadheim, H. Wischnewski, S. Wildt, T. U. Gerngross, Science 2003, 301, 1244. Elegant in vitro misacylated tRNA systems may also facilitate powerful biological glycoprotein synthesis; see: R. R. Schmidt, J. C. Castro-Palomino, O. Retz, Pure Appl. Chem. 1999, 71, 729.
    • (1999) Pure Appl. Chem. , vol.71 , pp. 729
    • Schmidt, R.R.1    Castro-Palomino, J.C.2    Retz, O.3
  • 28
    • 4544263216 scopus 로고    scopus 로고
    • note
    • The reactions of thiols with unsymmetrical disulfides, in contrast to selenenylsulfides, are often slow and nonselective, typically require a large excess of the thiol, and lead to the release of thiol(ate), which may serve to cleave any disulfide formed. Reactions with selenenylsulfides are typically fast, favor S-S formation from S-Se through disproportionation, and release a selenate, which does not compete in the reaction.
  • 29
    • 0000556811 scopus 로고
    • For examples of the behavior of S as an electrophile in S-Se-containing compounds, see: G. Bergson, G. Nordstrom, Ark. Kemi 1961, 17, 569; J. L. Kice, T. W. S. Lee, J. Am. Chem. Soc. 1978, 100, 5094; H. Fischer, N. Dereu, Bull. Soc. Chim. Belg. 1987, 96, 757. This reaction may compete with reaction at the electrophilic Se atom. However, reaction at the Se center would simply lead to in situ generation of glyco-SeS reagents, which would then feed into the same glycosylation sequence and ultimately lead to the required disproportionation of S-Se to S-S.
    • (1961) Ark. Kemi , vol.17 , pp. 569
    • Bergson, G.1    Nordstrom, G.2
  • 30
    • 33947092792 scopus 로고
    • For examples of the behavior of S as an electrophile in S-Se-containing compounds, see: G. Bergson, G. Nordstrom, Ark. Kemi 1961, 17, 569; J. L. Kice, T. W. S. Lee, J. Am. Chem. Soc. 1978, 100, 5094; H. Fischer, N. Dereu, Bull. Soc. Chim. Belg. 1987, 96, 757. This reaction may compete with reaction at the electrophilic Se atom. However, reaction at the Se center would simply lead to in situ generation of glyco-SeS reagents, which would then feed into the same glycosylation sequence and ultimately lead to the required disproportionation of S-Se to S-S.
    • (1978) J. Am. Chem. Soc. , vol.100 , pp. 5094
    • Kice, J.L.1    Lee, T.W.S.2
  • 31
    • 84989491409 scopus 로고
    • For examples of the behavior of S as an electrophile in S-Se-containing compounds, see: G. Bergson, G. Nordstrom, Ark. Kemi 1961, 17, 569; J. L. Kice, T. W. S. Lee, J. Am. Chem. Soc. 1978, 100, 5094; H. Fischer, N. Dereu, Bull. Soc. Chim. Belg. 1987, 96, 757. This reaction may compete with reaction at the electrophilic Se atom. However, reaction at the Se center would simply lead to in situ generation of glyco-SeS reagents, which would then feed into the same glycosylation sequence and ultimately lead to the required disproportionation of S-Se to S-S.
    • (1987) Bull. Soc. Chim. Belg. , vol.96 , pp. 757
    • Fischer, H.1    Dereu, N.2
  • 37
    • 4544246700 scopus 로고    scopus 로고
    • note
    • 2 (2 mM); pH 9.5). The thio sugar 4a (Glc-SH; 20 equiv) was added as a solution in water to the solution of the protein, and the mixture was placed on an end-over-end rotator. After 1 h the reaction was analyzed by mass spectrometry.
  • 38
    • 4544351140 scopus 로고    scopus 로고
    • note
    • A comparable glycosylation with iodoacetamides may take as long as 24 h: see reference [16].
  • 39
    • 0041430569 scopus 로고    scopus 로고
    • For more information, see Supporting Information
    • Considerably smaller quantities of the reagent (1-20 equiv) are required than typically used in protein glycosylation or protein modification (often of the order of 1000 equiv); see: B. G. Davis, Curr. Opin. Biotechnol. 2003, 14, 379. For more information, see Supporting Information.
    • (2003) Curr. Opin. Biotechnol. , vol.14 , pp. 379
    • Davis, B.G.1
  • 40
    • 4544374594 scopus 로고    scopus 로고
    • For further details, see Supporting Information
    • For further details, see Supporting Information.
  • 42
    • 4544367383 scopus 로고    scopus 로고
    • note
    • Attempted deprotection of the acetylated Glyco-SeS reagents only resulted in degradation.
  • 44
    • 4544231331 scopus 로고    scopus 로고
    • For further details, see Supporting Information
    • For further details, see Supporting Information.
  • 45
    • 4544294706 scopus 로고    scopus 로고
    • note
    • 2 buffer (0.05 M, 1.0 mL). The mixture was incubated for 40 min with UDP-Gal (1.6 mM) and recombinant bovine beta-1,4-galactosyltransferase (100 mU, Calbiochem) prior to analysis by mass spectrometry.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.