519002-35-8

Basic information

• Product Name: 7-Octen-2-one, 3-hydroxy-, (3R)- (9CI)
• Synonyms: 7-Octen-2-one, 3-hydroxy-, (3R)- (9CI)
• CAS NO: 519002-35-8
• Molecular Formula: C₈H₁₄O₂
• Molecular Weight: 142.19556
• Product Categories: ACETYLGROUP
• Mol File: 519002-35-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 7-Octen-2-one, 3-hydroxy-, (3R)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Octen-2-one, 3-hydroxy-, (3R)- (9CI)(519002-35-8)
• EPA Substance Registry System: 7-Octen-2-one, 3-hydroxy-, (3R)- (9CI)(519002-35-8)

Safety Data

• Hazardous Substances Data: 519002-35-8(Hazardous Substances Data)

Upstream product

• 118235-30-6 2-trimethylsilyloxyocta-2,7-diene 

Relevant articles and documents

Sanglifehrin-cyclophilin interaction: Degradation work, synthetic macrocyclic analogues, x-ray crystal structure, and binding data

Sanglifehrin A (SFA) is a novel immunosuppressive natural product isolated from Streptomyces sp. A92-308110. SFA has a very strong affinity for cyclophilin A (IC50 = 6.9 ± 0.9 nM) but is structurally different from cyclosporin A (CsA) and exerts its immunosuppressive activity via a novel mechanism. SFA has a complex molecular structure consisting of a 22-membered macrocycle, bearing in position 23 a nine-carbon tether terminated by a highly substituted spirobicyclic moiety. Selective oxidative cleavage of the C26 = C27 exocyclic double bond affords the spirolactam containing fragment 1 and macrolide 2. The affinity of 2 for cyclophilin (IC50 = 29 ± 2.1 nM) is essentially identical to SFA, which indicates that the interaction between SFA and cyclophilin A is mediated exclusively by the macrocyclic portion of the molecule. This observation was confirmed by the x-ray crystal structure resolved at 2.1 A of cyclophilin A complexed to macrolide 16, a close analogue of 2. The x-ray crystal structure showed that macrolide 16 binds to the same deep hydrophobic pocket of cyclophilin A as CsA. Additional valuable details of the structure-activity relationship were obtained by two different chemical approaches: (1) degradation work on macrolide 2 or (2) synthesis of a library of macrolide analogues using the ring-closing metathesis reaction as the key step. Altogether, it appears that the complex macrocyclic fragment of SFA is a highly optimized combination of multiple functionalities including an (E,E)-diene, a short polypropionate fragment, and an unusual tripeptide unit, which together provide an extremely strong affinity for cyclophilin A.