Total synthesis of arylomycin A2, a signal peptidase I (SPase I) inhibitor
2008
Abstract
A concise total synthesis of arylomycin A2 was accomplished featuring a key intramol. Suzuki-Miyaura reaction for the formation of the 14-membered meta,meta-cyclophane and direct coupling of a fully elaborated peptide side-chain with the macrocyclic core. [on SciFinder (R)]
Details
Title
Total synthesis of arylomycin A2, a signal peptidase I (SPase I) inhibitor
Author(s)
Dufour, Jeremy ; Neuville, Luc ; Zhu, Jieping
Published in
Synlett
Issue
15
Pages
2355-2359
Date
2008
ISSN
0936-5214
Keywords
Suzuki coupling reaction (intramol.; Suzuki-Miyaura; total synthesis of signal peptidase I inhibitor arylomycin A2 via intramol. Suzuki-Miyaura reaction); Macrocyclization (total synthesis of signal peptidase I inhibitor arylomycin A2 via intramol. Suzuki-Miyaura reaction); arylomycin A2 signal peptidase I inhibitor total synthesis; tripeptide prepn intramol Suzuki Miyaura macrocyclization
Note
CAN 150:6038
34-3
Amino Acids, Peptides, and Proteins
Institute de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
65979-36-4 (Signal peptidase I) Role: NUU (Other use, unclassified), USES (Uses) (inhibitors of; total synthesis of signal peptidase I inhibitor arylomycin A2 via intramol. Suzuki-Miyaura reaction); 2724-56-3 (Isolauric acid); 15761-38-3; 32462-30-9 (L-4-Hydroxyphenylglycine); 47173-80-8; 67706-14-3; 73183-34-3; 113850-71-8 Role: RCT (Reactant), RACT (Reactant or reagent) (total synthesis of signal peptidase I inhibitor arylomycin A2 via intramol. Suzuki-Miyaura reaction); 69651-48-5P; 193085-38-0P; 872414-47-6P; 1004524-53-1P; 1004524-61-1P; 1086702-96-6P; 1086702-98-8P; 1086703-01-6P; 1086703-03-8P; 1086703-05-0P; 1086703-08-3P; 1086703-10-7P; 1086703-14-1P; 1086703-19-6P; 1086703-22-1P; 1086703-24-3P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (total synthesis of signal peptidase I inhibitor arylomycin A2 via intramol. Suzuki-Miyaura reaction); 459844-20-3P (Arylomycin A2); 1086703-12-9P Role: SPN (Synthetic preparation), PREP (Preparation) (total synthesis of signal peptidase I inhibitor arylomycin A2 via intramol. Suzuki-Miyaura reaction)
34-3
Amino Acids, Peptides, and Proteins
Institute de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
65979-36-4 (Signal peptidase I) Role: NUU (Other use, unclassified), USES (Uses) (inhibitors of; total synthesis of signal peptidase I inhibitor arylomycin A2 via intramol. Suzuki-Miyaura reaction); 2724-56-3 (Isolauric acid); 15761-38-3; 32462-30-9 (L-4-Hydroxyphenylglycine); 47173-80-8; 67706-14-3; 73183-34-3; 113850-71-8 Role: RCT (Reactant), RACT (Reactant or reagent) (total synthesis of signal peptidase I inhibitor arylomycin A2 via intramol. Suzuki-Miyaura reaction); 69651-48-5P; 193085-38-0P; 872414-47-6P; 1004524-53-1P; 1004524-61-1P; 1086702-96-6P; 1086702-98-8P; 1086703-01-6P; 1086703-03-8P; 1086703-05-0P; 1086703-08-3P; 1086703-10-7P; 1086703-14-1P; 1086703-19-6P; 1086703-22-1P; 1086703-24-3P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (total synthesis of signal peptidase I inhibitor arylomycin A2 via intramol. Suzuki-Miyaura reaction); 459844-20-3P (Arylomycin A2); 1086703-12-9P Role: SPN (Synthetic preparation), PREP (Preparation) (total synthesis of signal peptidase I inhibitor arylomycin A2 via intramol. Suzuki-Miyaura reaction)
Laboratories
LSPN
Record Appears in
Scientific production and competences > SB - School of Basic Sciences > ISIC - Institute of Chemical Sciences and Engineering > LSPN - Laboratory of synthesis and natural products
Peer-reviewed publications
Work outside EPFL
Journal Articles
Published
Peer-reviewed publications
Work outside EPFL
Journal Articles
Published
Record creation date
2010-11-25