메뉴 건너뛰기




Volumn 15, Issue 43, 2009, Pages 11444-11449

A new ligation strategy for peptide and protein glycosylation: Photoinduced thiol-ene coupling

Author keywords

Alkynes; Glycoproteins; Glycosylation; Protein modification; Thiols

Indexed keywords

ALKENYL; ALKYNES; ANOMERIC LINKAGES; C-GLYCOSIDES; COUPLING REACTION; GLYCOPEPTIDES; GLYCOSYL AMINO ACIDS; HYDROTHIOLATION; PHOTO-INDUCED; PHOTOINDUCED COUPLING; PROTEIN GLYCOSYLATION; PROTEIN MODIFICATION; RADICAL MECHANISM; REACTION PARTNERS; REGIO-SELECTIVE; SITE-SPECIFIC; SULFHYDRYL GROUPS; THIOL-ENE COUPLING; THIOLS;

EID: 70350509098     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200901746     Document Type: Article
Times cited : (123)

References (71)
  • 1
    • 70350517983 scopus 로고    scopus 로고
    • (Eds.: A. Varki, R. D. Cummings, J. D. Esko, H. H. Freeze, G. W Hart, J. Marth), Cold Spring Harbor Laboratory, New York, Chapters 8
    • J. Marth, B. Lowe, A. Varki in Essentials of Glycobiology (Eds.: A. Varki, R. D. Cummings, J. D. Esko, H. H. Freeze, G. W Hart, J. Marth), Cold Spring Harbor Laboratory, New York, 1999, Chapters 8;
    • (1999) Essentials of Glycobiology
    • Marth, J.1    Lowe, B.2    Varki, A.3
  • 2
    • 70350520917 scopus 로고    scopus 로고
    • Eds.: A. Varki, R. D. Cummings, J. D. Esko, H. H. Freeze, G. W. Hart, J. Marth, Cold Spring Harbor Laboratory, New York, Chapters 17
    • J. Marth, B. Lowe, A. Varki in Essentials of Glycobiology (Eds.: A. Varki, R. D. Cummings, J. D. Esko, H. H. Freeze, G. W. Hart, J. Marth), Cold Spring Harbor Laboratory, New York, 1999, Chapters 17;
    • (1999) Essentials of Glycobiology
    • Marth, J.1    Lowe, B.2    Varki, A.3
  • 6
    • 0039174268 scopus 로고    scopus 로고
    • Review: O. Seitz, ChemBioChem 2000,1, 214-246.
    • (2000) ChemBioChem , vol.1 , pp. 214-246
    • Seitz, O.1
  • 8
    • 0001094662 scopus 로고    scopus 로고
    • b) R. A. Dwek, Chem. Rev. 1996, 96, 683-720;
    • (1996) Chem. Rev. , vol.96 , pp. 683-720
    • Dwek, R.A.1
  • 15
    • 0036462604 scopus 로고    scopus 로고
    • c) B. G. Davis, Chem. Rev. 2002, 102, 579-601;
    • (2002) Chem. Rev. , vol.102 , pp. 579-601
    • Davis, B.G.1
  • 25
    • 46749125397 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 4411-4415;
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 4411-4415
  • 29
    • 34548764429 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 6849-6851.
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 6849-6851
  • 32
    • 41049108991 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 2244-2247.
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 2244-2247
  • 36
  • 38
    • 57749121492 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 10030-10074. For a recent article, see:
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 10030-10074
  • 40
    • 61349200075 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 1729-1731.
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 1729-1731
  • 44
    • 66749108086 scopus 로고    scopus 로고
    • For a brief commentary on the potential of this reaction in synthesis, see: A. Dondoni, Angew. Chem. 2008, 120, 9133-9135;
    • (2008) Angew. Chem. , vol.120 , pp. 9133-9135
    • Dondoni, A.1
  • 45
    • 56249095812 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 8995-8997.
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 8995-8997
  • 48
    • 34447328219 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 5226-5230.
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 5226-5230
  • 49
    • 66249087981 scopus 로고    scopus 로고
    • M. Fiore, A. Marra, A. Dondoni, J. Org. Chem. 2009, 74, 4422-4425. For further applications of TEC in bioorganic chemistry, see references therein.
    • (2009) J. Org. Chem. , vol.74 , pp. 4422-4425
    • Fiore, M.1    Marra, A.2    Dondoni, A.3
  • 51
    • 46749155086 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 4421-4424.
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 4421-4424
  • 52
    • 0035804940 scopus 로고    scopus 로고
    • The thiol-ene reaction between N-allyl glycosides and cysteamine was reported by Klaffke and co-workers: D. Ramos, P. Rollin, W. Klaffke, J. Org. Chem. 2001, 66, 2948-2956.
    • (2001) J. Org. Chem. , vol.66 , pp. 2948-2956
    • Ramos, D.1    Rollin, P.2    Klaffke, W.3
  • 56
    • 70350510692 scopus 로고    scopus 로고
    • note
    • 2 at room temperature.
  • 58
    • 70350514338 scopus 로고    scopus 로고
    • This compound was kindly provided as trifluoroacetic salt by UFPeptides s.r.L. (University of Ferrara)
    • This compound was kindly provided as trifluoroacetic salt by UFPeptides s.r.L. (University of Ferrara).
  • 59
    • 70350488746 scopus 로고    scopus 로고
    • note
    • Surprisingly, the use of lower amounts of DPAP (50 and 10mol%) were not sufficient for achieving a complete glycosylation of this peptide.
  • 61
    • 70350493553 scopus 로고    scopus 로고
    • note
    • Max = 254nm, 70W) solutions of BSA and sugar la in DMSO-phosphate buffer (pH 7.4) for 3-6 h either in the absence or presence of 4,4'-azobis(4cyanovaleric acid) as the sensitizer.
  • 64
    • 50249180373 scopus 로고    scopus 로고
    • Indeed, the detected mass shift was lower than the value calculated for the addition of three sugar units (3x372 uma). This result is explained by the presence of a portion of 10 containing two galactose units only. As commonly observed for partially oxidized commercial batches of BSA, the BSA subjected to functionalization with la contained only a fraction of available free sulfhydryl groups at Cys34 (ca. 45% from previous studies: a) P. De, M. Li, S. R. Gondi, S. B. Sumerlin, J. Am. Chem. Soc. 2008, 130, 11288-11289;
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 11288-11289
    • De, P.1    Li, M.2    Gondi, S.R.3    Sumerlin, S.B.4
  • 66
    • 51649115626 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2008, 47, 6263-6266).
    • (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 6263-6266
  • 67
    • 70350496412 scopus 로고    scopus 로고
    • note
    • Unfortunately, pre-treatment of glycosylated BSA 10 with dithiothreitol (DTT) for protein disulfide bonds reduction followed by excess iodoacetamide (IAA) sulfhydryl groups derivatization produced tryptic fragments, which displayed the acetamido group at cysteine residues 34, 75, and, very likely, at Cys-91 in place of the expected galactoside moiety (see the Supporting Information). This outcome is tentatively explained by the formation of intermediate S-acetamido sulfonium derivatives of glycosylated cysteine peptide fragments followed by a β-elimination process, which should result in the formation of the allyl galactoside la and S-acetamido peptide fragments (see Scheme S1). The occurrence of this undesired side reaction that makes the DTT/IAA analysis method unsuitable for the characterization of glycosylated BSA 10 was also demonstrated by using the less complex glycopeptide 9 as the substrate (Supporting Information). For a deeper discussion on the β-elimination reaction of dialkylated sulfonium derivatives of Cys and the synthetic potential of related oxidative elimination of Cys for protein modification, see ref. [8].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.