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Volumn 64, Issue 13, 1999, Pages 4574-4575

Stereoselective backbone modifications of peptides via chelate enolate Claisen rearrangement

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; AMINO ACID; GLYCINE; LEAD; MANGANESE; PEPTIDE;

EID: 0033603455     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9904821     Document Type: Article
Times cited : (51)

References (36)
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    • Seebach, D.1
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    • (1998) Angew. Chem. , vol.110 , pp. 1722-1743
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  • 27
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    • and references therein
    • For a recent review on metal complexes of amino acids and peptides see: Severin, K.; Bergs, R.; Beck, W. Angew. Chem. 1998, 110, 1722-1743; Angew. Chem., Int. Ed. 1998, 37, 1634-1664 and references therein.
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 1634-1664
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    • note
    • The crotyl esters were chosen, because they allow the generation of two stereogenic centers in a highly diagtereoselective fashion (95% ds), as determined by HPLC or GC.
  • 29
    • 0344882205 scopus 로고    scopus 로고
    • note
    • Titanium compounds are known to catalyze transesterifications. This can explain the lower yields obtained in some cases (see also ref 11).
  • 30
    • 0345313270 scopus 로고    scopus 로고
    • note
    • Using cinnamyl esters, elimination of cinnamyl alcohol was observed as a side reaction.
  • 31
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    • note
    • Comparable lithium chelate complexes were proposed by Seebach et al. to explain the solubilization of peptides in the presence of lithium salts (ref 4).
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    • note
    • HPLC analyses were performed on the corresponding methyl esters using a achiral column (silica gel) and a chiral column (Daicel OD-H) as well.
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    • Kazmaier, U.; Krebs, A. Angew. Chem. 1995, 107, 2213; Angew. Chem., Int. Ed. Engl. 1995, 34, 2012.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.