메뉴 건너뛰기




Volumn 2, Issue 8, 2000, Pages 1105-1107

A new selective synthesis of the lle-allo-Thr-Gly tripeptide fragment of lysobactin

Author keywords

[No Author keywords available]

Indexed keywords

DEPSIPEPTIDE; LYSOBACTIN; OLIGOPEPTIDE; PEPTIDE FRAGMENT;

EID: 0034689875     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005659o     Document Type: Article
Times cited : (27)

References (22)
  • 12
    • 84985656312 scopus 로고
    • For a review of aziridine-containing peptides, see: (a) Okawa, K.; Nakajima, K. Biopolymers 1981, 20, 1811-1821.
    • (1981) Biopolymers , vol.20 , pp. 1811-1821
    • Okawa, K.1    Nakajima, K.2
  • 16
    • 0042751439 scopus 로고    scopus 로고
    • note
    • 3).
  • 17
    • 0043252551 scopus 로고    scopus 로고
    • note
    • It is generally assumed that the ring expansion of N-acylaziridine occurs via a carbocationic-like TS (ref 3a) or a carbocationic intermediate (ref 3b) and is favored by the presence of Lewis acids. (equation presented) Our semiempirical calculations suggest that the presence of the imidazolidin-2-one substituent could be responsible for the accelerated expansion rate. Indeed, the reactant adopts a preferential conformation in which the endocyclic carbonylic oxygen points toward the aziridine C3′, thus stabilizing the incipient positive charge. This model is in accord with our previous experimental observations that aziridine 2-ester ring expansion is much slower than that of aziridine 2-imide.
  • 20
    • 0042250033 scopus 로고    scopus 로고
    • note
    • 3).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.