Primary-Amine-Specific Lactamization of ω-Amino Acids by an Artificial Cyclotransferase Based on [18]Crown-6

Feet first: Carboxylic acids with a primary amino group in the farthest position from the carboxy group are specifically bound to an artificial cyclotransferase based on [18]crown‐6. The amino group fits into the [18]crown‐6 substrate‐binding site to bring the carboxyl group close to the 2‐ammonio‐1...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2006-02, Vol.45 (8), p.1252-1255
Main Authors: Kunishima, Munetaka, Hioki, Kazuhito, Moriya, Takahiro, Morita, Jun, Ikuta, Tomoko, Tani, Shohei
Format: Article
Language:English
Subjects:
Amines - chemistry
Amino Acids - chemistry
Amino Acids - metabolism
condensation
crown compounds
Crown Compounds - chemistry
Crown Compounds - metabolism
Cyclization
enzyme models
lactams
Lactams - chemistry
Metals - chemistry
Molecular Structure
transferases
Transferases - metabolism
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Summary:Feet first: Carboxylic acids with a primary amino group in the farthest position from the carboxy group are specifically bound to an artificial cyclotransferase based on [18]crown‐6. The amino group fits into the [18]crown‐6 substrate‐binding site to bring the carboxyl group close to the 2‐ammonio‐1,3,5‐triazine reaction site for selective conversion into a lactam.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200504027