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Volumn 44, Issue 15, 2005, Pages 2215-2220

Head-to-tail peptide cyclodimerization by copper-catalyzed azide-alkyne cycloaddition

Author keywords

Alkynes; Azides; Cycloaddition; Dimerization; Peptides

Indexed keywords

CATALYSIS; COPPER; DIMERIZATION; POLYPEPTIDES; POLYSTYRENES;

EID: 17644409095     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200461656     Document Type: Article
Times cited : (198)

References (47)
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    • note
    • For details, see Supporting Information.
  • 37
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    • The use of azide and alkyne connecting groups avoids certain protecting group problems commonly encountered in solid phase peptide synthesis. For example, orthogonal protection was required for an aspartate residue of resin-3 to prepare for cyclization by amide bond formation. The 4-(N-(1-(4,4-dimethyl-2, 6-dioxocyclohexylidene)-3-methylbutyl)amino)benzyl ester (Dmab) group, most commonly used in such situations, is expensive, bulky, and chemically sensitive: T. Johnson, M. Liley, T. J. Cheeseright, F. Begum, J. Chem. Soc. Perkin Trans. 1 2000, 2811-2820. The introduction and manipulation of aspartate can give rise to undesired aspartamide cyclization with neighboring residues during both Fmoc and Boc synthetic approaches and piperidide formation during Fmoc manipulations; deprotection is often relatively difficult. The standard solutions to these difficulties (such as protecting the preceding residue as N-Hmb; Hmb = 2-hydroxy-4-methoxybenzyl) are also somewhat cumbersome. Each of these problems were encountered in the synthesis and isolation of cyclo-3, but did not occur in the preparation and reactions of the analogous sequence 1.
    • (2000) J. Chem. Soc. Perkin Trans. 1 , pp. 2811-2820
    • Johnson, T.1    Liley, M.2    Cheeseright, T.J.3    Begum, F.4
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    • See the preceding Communication in this issue: V. O. Rodionov, V. V. Fokin, M. G. Finn, Angew. Chem. 2005, 117, 2250; Angew. Chem. Int. Ed. 2005, 44, 2210 (DOI: 10.1002/anie.200461496).
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    • Rodionov, V.O.1    Fokin, V.V.2    Finn, M.G.3
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    • DOI: 10.1002/anie.200461496
    • See the preceding Communication in this issue: V. O. Rodionov, V. V. Fokin, M. G. Finn, Angew. Chem. 2005, 117, 2250; Angew. Chem. Int. Ed. 2005, 44, 2210 (DOI: 10.1002/anie.200461496).
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 2210
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    • The formation of peptide dimers with copper(II) by interaction with backbone amide nitrogen atoms has been described: H. Yokoi, A. Hanaki, Chem. Lett. 1983, 8, 1319-1322. This is, of course, different from copper(I), for which many protein interactions are known, but all involve anchoring to at least one "soft" side-chain ligand.
    • (1983) Chem. Lett. , vol.8 , pp. 1319-1322
    • Yokoi, H.1    Hanaki, A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.