메뉴 건너뛰기




Volumn 45, Issue 3, 2006, Pages 477-481

Efficient solid-phase lipopeptide synthesis employing the ellman sulfonamide linker

Author keywords

Lipids; Peptides; Solid phase synthesis; Sulfonamides

Indexed keywords

SOLID-PHASE SYNTHESIS; SULFONAMIDES;

EID: 30444432217     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200503298     Document Type: Article
Times cited : (29)

References (40)
  • 3
    • 0005759204 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2000, 39, 4193-4214.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 4193-4214
  • 6
    • 0037099479 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2002, 41, 2546-2550;
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 2546-2550
  • 8
    • 4544333147 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2004, 43, 2711-2714;
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 2711-2714
  • 12
    • 0035857550 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2001, 40, 1056-1058.
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 1056-1058
  • 16
    • 8844266021 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2004, 43, 5839-5842;
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 5839-5842
  • 25
    • 0037019977 scopus 로고    scopus 로고
    • We have repeatedly observed that after oxidative cleavage of the hydrazide linker major fractions of the synthesized lipopeptides remained bound to the solid support by means of an unidentified linkage that could not be cleaved oxidatively or under acidic or basic conditions anymore. The oxidative cleavage of the hydrazide linker most probably proceeds through an intermediate acyl radical (see: M. Völkert, S. Koul, G. H. Müller, M. Lehnig, H. Waldmann, J. Org. Chem. 2002, 67, 6902-6910) that may form a covalent bond with the polymeric support.
    • (2002) J. Org. Chem. , vol.67 , pp. 6902-6910
    • Völkert, M.1    Koul, S.2    Müller, G.H.3    Lehnig, M.4    Waldmann, H.5
  • 26
    • 2942525475 scopus 로고    scopus 로고
    • Numerous attempts to trap such an intermediate under the conditions of release from the solid support were, however, fruitless (for a related observation, see: J. A. Camarero, B. J. Hackel, J. J. de Yorco, A. R. Mitchell, J. Org. Chem. 2004, 69, 4145-4151).
    • (2004) J. Org. Chem. , vol.69 , pp. 4145-4151
    • Camarero, J.A.1    Hackel, B.J.2    De Yorco, J.J.3    Mitchell, A.R.4
  • 32
    • 30444456629 scopus 로고    scopus 로고
    • see ref. [7c]
    • The compatibility of methionine and Cys(Trt) with the conditions for the cleavage of the Ellman linker has been described before, see ref. [7c]
  • 34
    • 0035896201 scopus 로고    scopus 로고
    • Serine side chains were protected as trityl ethers, lysine side chains were masked with the methyltrityl (Mtt) group. The side-chain protecting groups were removed from the peptides by treatment with TFA/triethylsilane/ dichloromethane (1:2:97) for 2 h after the release of the peptides from the solid support (see D. Kadereit, P. Deck, I. Heinemann, H. Waldmann, Chem. Eur. J. 2001, 7, 1184-1193).
    • (2001) Chem. Eur. J. , vol.7 , pp. 1184-1193
    • Kadereit, D.1    Deck, P.2    Heinemann, I.3    Waldmann, H.4
  • 35
    • 30444438644 scopus 로고    scopus 로고
    • note
    • In further experiments, it was shown that a BODIPY fluorophore can also be introduced at the C terminus of lipidated peptides by nucleophilic trapping of the activated sulfonamide with the BODIPY-2-aminoethyl amide (data not shown).
  • 37
    • 0034771776 scopus 로고    scopus 로고
    • and references therein
    • b) S. Cockcroft, Cell. Mol. Life Sci. 2001, 58, 1674-1687, and references therein.
    • (2001) Cell. Mol. Life Sci. , vol.58 , pp. 1674-1687
    • Cockcroft, S.1
  • 39
    • 0034678780 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2000, 39, 1449-1453;
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 1449-1453


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.