The structural requirements for inhibition of proteasome function by the lactacystin-derived β-lactone and synthetic analogs

Tetrahedron

Volumn 55, Issue 11, 1999, Pages 3305-3316

  Corey, E J ^a   Li, Wei Dong Z ^a   Nagamitsu, Tohru ^a   Fenteany, Gabriel ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYSTINE; LACTONE; PROTEASOME;

ARTICLE; ENZYME INHIBITION; INHIBITION KINETICS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 0033104464     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)01142-9     Document Type: Article

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21. In this β-lactonization and in each of the others reported herein it was not necessary to protect the C(9)- hydroxyl since β-lactone formation occurred exclusively at the C(6)-hydroxyl. This highly selective β-lactonization to form the 5/4 fused β-lactone is the result of favorable entropie and steric factors.
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