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Volumn 2, Issue 1, 2005, Pages 59-81

Recent carbohydrate-based chemoselective ligation applications

Author keywords

Chemoselective ligation; Cycloadditions; Diels alder reactions; Oligosaccharides

Indexed keywords


EID: 23644450919     PISSN: 15701794     EISSN: None     Source Type: Journal    
DOI: 10.2174/1570179052996937     Document Type: Review
Times cited : (76)

References (212)
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    • Muir, T.W.; Williams, M.J.; Ginsberg, M.H.; Kent, S.B.H. Biochemistry 1994, 33, 7701-7708; c Rose, K. J. Am. Chem. Soc. 1994, 116, 30-33.
    • b) Muir, T.W.; Williams, M.J.; Ginsberg, M.H.; Kent, S.B.H. Biochemistry 1994, 33, 7701-7708; c) Rose, K. J. Am. Chem. Soc. 1994, 116, 30-33.
  • 10
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    • Many chemoselective ligation reactions, like azide/alkyne Huisgen 1,3-dipolar cycloadditions, fall under the umbrella of click chemistry, a concept developed and popularized by Sharpless and coworkers (see ref 6, However, it should be noted that chemoselective ligation and click chemistry are not mutually inclusive and are defined based on somewhat different criteria, Chemoselective ligation emerged from biological chemistry and therefore the concept embodies the need to form stable covalent bonds between molecular fragments under physiological conditions (aqueous, narrow pH range, functional group tolerance, mild temperatures, Click chemistry is an ideal that refers to a class of selective, covalent bond-formating reactions that have a large thermodynamic driving force and must a) provide high yields and clean products, b) employ benign, easily removable solvents (or no solvent, c) tolerate the presence of air and ideally water. Click chemist
    • Many chemoselective ligation reactions - like azide/alkyne Huisgen 1,3-dipolar cycloadditions - fall under the umbrella of "click chemistry," a concept developed and popularized by Sharpless and coworkers (see ref 6). However, it should be noted that chemoselective ligation and click chemistry are not mutually inclusive and are defined based on somewhat different criteria, Chemoselective ligation emerged from biological chemistry and therefore the concept embodies the need to form stable covalent bonds between molecular fragments under physiological conditions (aqueous, narrow pH range, functional group tolerance, mild temperatures). "Click chemistry" is an ideal that refers to a class of selective, covalent bond-formating reactions that have a large thermodynamic driving force and must a) provide high yields and clean products, b) employ benign, easily removable solvents (or no solvent), c) tolerate the presence of air and ideally water. Click chemistry does not necessarily suggest the need to carry out reactions in a certain environment.
  • 13
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    • For reviews that discuss the chemoselective nature of Huisgen 1,3-dipolar cycloadditions and resulting applications see a Kolb, H.C.; Finn, M.G.; Sharpless, K.B. Angew. Chem. Int. Ed. 2001, 40, 2004-2021;
    • For reviews that discuss the chemoselective nature of Huisgen 1,3-dipolar cycloadditions and resulting applications see a) Kolb, H.C.; Finn, M.G.; Sharpless, K.B. Angew. Chem. Int. Ed. 2001, 40, 2004-2021;
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    • Staudinger, H.; Meyer, J. Helv. Chem. Acta 1919, 2, 635-646. Reviews: a Gololobov, Y.G.; Zhmurova, I.N.; Kasukhin, L.F. Tetrahedron 1981, 37, 437-472;
    • Staudinger, H.; Meyer, J. Helv. Chem. Acta 1919, 2, 635-646. Reviews: a) Gololobov, Y.G.; Zhmurova, I.N.; Kasukhin, L.F. Tetrahedron 1981, 37, 437-472;
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    • For a recent review see
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    • For recent reviews, see a
    • For recent reviews, see a) Hirabayashi, J. Trends Biotechnol. 2003, 21, 141-143;
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  • 52
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    • Reviews: a
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    • Gonzalez et al. have used 1,3-dipolar cycloaddition reactions between alkynes and azides or nitrile oxides to assemble multivalent neoglycoconjugates. These reactions were conducted using protected sugars in organic solvent and therefore do not strictly qualify as chemoselective ligation reactions, see a Perez-Balderas, F.; Ortega-Munoz, M.; Morales-Sanfrutos, J.; Hernandez-Mateo, F.; Calvo-Flores, F. G.; Calvo-Asin, J. A.; Isac-Garcia, J.; Santoyo-Gonzalez, F. Org. Lett. 2003, 5, 1951-1954;
    • Gonzalez et al. have used 1,3-dipolar cycloaddition reactions between alkynes and azides or nitrile oxides to assemble multivalent neoglycoconjugates. These reactions were conducted using protected sugars in organic solvent and therefore do not strictly qualify as chemoselective ligation reactions, see a) Perez-Balderas, F.; Ortega-Munoz, M.; Morales-Sanfrutos, J.; Hernandez-Mateo, F.; Calvo-Flores, F. G.; Calvo-Asin, J. A.; Isac-Garcia, J.; Santoyo-Gonzalez, F. Org. Lett. 2003, 5, 1951-1954;
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    • Bertozzi, C.R., December 2003, unpublished results, Ann. Meeting Sec. for Glycobiol.
    • Bertozzi, C.R., December 2003, unpublished results, Ann. Meeting Sec. for Glycobiol.
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    • Thorson, J.S.; Vogt, T. Glycosylated Natural Products in Carbohydrate-based Drug Discovery;
    • d) Thorson, J.S.; Vogt, T. Glycosylated Natural Products in Carbohydrate-based Drug Discovery;
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.