-
1
-
-
0034887203
-
-
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
-
-
J. B. Lowe, Cell 2001, 104, 809.
-
(2001)
Cell
, vol.104
, pp. 809
-
-
Lowe, J.B.1
-
9
-
-
0023893055
-
-
T. W. Rademacher, R. B. Parekh, R. A. Dwek, Annu. Rev. Biochem. 1988, 57, 785.
-
(1988)
Annu. Rev. Biochem.
, vol.57
, pp. 785
-
-
Rademacher, T.W.1
Parekh, R.B.2
Dwek, R.A.3
-
10
-
-
0042322600
-
-
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.
-
(2003)
Science
, vol.301
, pp. 1244
-
-
Hamilton, S.R.1
Bobrowicz, P.2
Bobrowicz, B.3
Davidson, R.C.4
Li, H.5
Mitchell, T.6
Nett, J.H.7
Rausch, S.8
Stadheim, T.A.9
Wischnewski, H.10
Wildt, S.11
Gerngross, T.U.12
-
11
-
-
0000962459
-
-
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
-
12
-
-
0028902241
-
-
R. S. Rush, P. L. Derby, D. M. Smith, C. Merry, G. Rogers, M. F. Rohde, V. Katta, Anal. Chem. 1995, 67, 1442.
-
(1995)
Anal. Chem.
, vol.67
, pp. 1442
-
-
Rush, R.S.1
Derby, P.L.2
Smith, D.M.3
Merry, C.4
Rogers, G.5
Rohde, M.F.6
Katta, V.7
-
13
-
-
0025893335
-
-
L. C. Wasley, G. Timony, P. Murtha, J. Stoudemire, A. J. Dorner, J. Caro, M. Krieger, R. J. Kaufman, Blood 1991, 77, 2624.
-
(1991)
Blood
, vol.77
, pp. 2624
-
-
Wasley, L.C.1
Timony, G.2
Murtha, P.3
Stoudemire, J.4
Dorner, A.J.5
Caro, J.6
Krieger, M.7
Kaufman, R.J.8
-
14
-
-
0035122538
-
-
C. King, R. Mueller Hoenger, M. Malo Cleary, K. Murali-Krishna, R. Ahmed, E. King, N. Sarvetnick, Nat. Med. 2001, 7, 206.
-
(2001)
Nat. Med.
, vol.7
, pp. 206
-
-
King, C.1
Mueller Hoenger, R.2
Malo Cleary, M.3
Murali-Krishna, K.4
Ahmed, R.5
King, E.6
Sarvetnick, N.7
-
16
-
-
0037442330
-
-
H. Liu, L. Wang, A. Brock, C. H. Wong, P. G. Schultz, J. Am. Chem. Soc. 2003, 125, 1702.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 1702
-
-
Liu, H.1
Wang, L.2
Brock, A.3
Wong, C.H.4
Schultz, P.G.5
-
17
-
-
0035057706
-
-
D. Macmillan, R. M. Bill, K. A. Sage, D. Fern, S. L. Flitsch, Chem. Biol. 2001, 8, 133.
-
(2001)
Chem. Biol.
, vol.8
, pp. 133
-
-
Macmillan, D.1
Bill, R.M.2
Sage, K.A.3
Fern, D.4
Flitsch, S.L.5
-
18
-
-
0033596308
-
-
Y. Shin, K. A. Winans, B. J. Backes, S. B. H. Kent, J. A. Ellman, C. R. Bertozzi, J. Am. Chem. Soc. 1999, 121, 11684.
-
(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 11684
-
-
Shin, Y.1
Winans, K.A.2
Backes, B.J.3
Kent, S.B.H.4
Ellman, J.A.5
Bertozzi, C.R.6
-
19
-
-
0030936614
-
-
K. Witte, P. Sears, R. Martin, C.-H. Wong, J. Am. Chem. Soc. 1997, 119, 2114.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 2114
-
-
Witte, K.1
Sears, P.2
Martin, R.3
Wong, C.-H.4
-
20
-
-
0032567423
-
-
B. G. Davis, R. C. Lloyd, J. B. Jones, J. Org. Chem. 1998, 63, 9614.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 9614
-
-
Davis, B.G.1
Lloyd, R.C.2
Jones, J.B.3
-
21
-
-
0034000336
-
-
B. G. Davis, M. A. T. Maughan, M. P. Green, A. Ullman, J. B. Jones, Tetrahedron: Asymmetry 2000, 11, 245.
-
(2000)
Tetrahedron: Asymmetry
, vol.11
, pp. 245
-
-
Davis, B.G.1
Maughan, M.A.T.2
Green, M.P.3
Ullman, A.4
Jones, J.B.5
-
22
-
-
0344982065
-
-
D. P. Gamblin, P. Garnier, S. J. Ward, N. J. Oldham, A. J. Fairbanks, B. G. Davis, Org. Biomol. Chem. 2003, 1, 3642.
-
(2003)
Org. Biomol. Chem.
, vol.1
, pp. 3642
-
-
Gamblin, D.P.1
Garnier, P.2
Ward, S.J.3
Oldham, N.J.4
Fairbanks, A.J.5
Davis, B.G.6
-
23
-
-
0033933620
-
-
B. G. Davis, R. C. Lloyd, J. B. Jones, Bioorg. Med. Chem. 2000, 8, 1527.
-
(2000)
Bioorg. Med. Chem.
, vol.8
, pp. 1527
-
-
Davis, B.G.1
Lloyd, R.C.2
Jones, J.B.3
-
27
-
-
0034705133
-
-
L. Zhong, E. S. J. Arnér, A. Holmgren, Proc. Natl. Acad. Sci. USA 2000, 97, 5854.
-
(2000)
Proc. Natl. Acad. Sci. USA
, vol.97
, pp. 5854
-
-
Zhong, L.1
Arnér, E.S.J.2
Holmgren, A.3
-
28
-
-
4544263216
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note
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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.
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29
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0000556811
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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.
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(1961)
Ark. Kemi
, vol.17
, pp. 569
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Bergson, G.1
Nordstrom, G.2
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30
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33947092792
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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
-
-
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
-
34
-
-
0032574793
-
-
G. DeSantis, P. Berglund, M. R. Stabile, M. Gold, J. B. Jones, Biochemistry 1998, 37, 5968.
-
(1998)
Biochemistry
, vol.37
, pp. 5968
-
-
DeSantis, G.1
Berglund, P.2
Stabile, M.R.3
Gold, M.4
Jones, J.B.5
-
37
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4544246700
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note
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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.
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38
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4544351140
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note
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A comparable glycosylation with iodoacetamides may take as long as 24 h: see reference [16].
-
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39
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0041430569
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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
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4544374594
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For further details, see Supporting Information
-
For further details, see Supporting Information.
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-
41
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0037039298
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K. L. Kiick, E. Saxon, D. A. Tirrell, C. R. Bertozzi, Proc. Natl. Acad. Sci. USA 2002, 99, 19.
-
(2002)
Proc. Natl. Acad. Sci. USA
, vol.99
, pp. 19
-
-
Kiick, K.L.1
Saxon, E.2
Tirrell, D.A.3
Bertozzi, C.R.4
-
42
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4544367383
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note
-
Attempted deprotection of the acetylated Glyco-SeS reagents only resulted in degradation.
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43
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33644811612
-
-
G. L. Ellman, K. D. Courtney, V. Andres, R. M. Featherstone, Biochem. Pharmacol. 1961, 7, 88.
-
(1961)
Biochem. Pharmacol.
, vol.7
, pp. 88
-
-
Ellman, G.L.1
Courtney, K.D.2
Andres, V.3
Featherstone, R.M.4
-
44
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4544231331
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For further details, see Supporting Information
-
For further details, see Supporting Information.
-
-
-
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45
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4544294706
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note
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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.
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-
-
-
47
-
-
0035847491
-
-
I. Shin, H.-j. Jung, M.-r. Lee, Tetrahedron Lett. 2001, 42, 1325.
-
(2001)
Tetrahedron Lett.
, vol.42
, pp. 1325
-
-
Shin, I.1
Jung, H.-J.2
Lee, M.-R.3
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