An enzymatic route to selenazolines

Jesko Koehnke; Falk Morawitz; Andrew F. Bent; Wael E. Houssen; Sally L. Shirran; Matthew A. Fuszard; Iain A. Smellie; Catherine H. Botting; Margaret C. M. Smith; Marcel Jaspars; James H. Naismith

doi:10.1002/cbic.201300037

An enzymatic route to selenazolines

Jesko Koehnke, Falk Morawitz, Andrew F. Bent, Wael E. Houssen, Sally L. Shirran, Matthew A. Fuszard, Iain A. Smellie, Catherine H. Botting, Margaret C. M. Smith, Marcel Jaspars^*, James H. Naismith

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

Abstract

Ringing the changes: Selenazolines have applications in medicinal chemistry, but their synthesis is challenging. We report a new convenient and less toxic route to these heterocycles that starts from commercially available selenocysteine. The new route depends on a heterocyclase enzyme that creates oxazolines and thiazolines from serines/threonines and cysteines.

Original language	English
Pages (from-to)	564-567
Number of pages	4
Journal	ChemBioChem
Volume	14
Issue number	5
DOIs	https://doi.org/10.1002/cbic.201300037
Publication status	Published - 18 Mar 2013

Keywords

Patellamides
Macrocyclization
Derivatives
Biochemistry
Line
Biosynthesis
Selenazolines

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10.1002/cbic.201300037

Koeknke2013ChemBioChem14-5-564
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This is an open access article.
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Exploring the mechanism: Exploring the mechanism and scope of the enzymatic formation of five membered ring
Naismith, J. (PI), Botting, C. H. (CoI), Koehnke, J. A. J. G. (CoI) & Schwarz-Linek, U. (CoI)
BBSRC
1/10/13 → 30/09/17
Project: Standard

Cite this

@article{ea84f969b4e14144b0a9c46a329c7094,

title = "An enzymatic route to selenazolines",

abstract = "Ringing the changes: Selenazolines have applications in medicinal chemistry, but their synthesis is challenging. We report a new convenient and less toxic route to these heterocycles that starts from commercially available selenocysteine. The new route depends on a heterocyclase enzyme that creates oxazolines and thiazolines from serines/threonines and cysteines.",

keywords = "Patellamides, Macrocyclization, Derivatives, Biochemistry, Line, Biosynthesis, Selenazolines",

author = "Jesko Koehnke and Falk Morawitz and Bent, {Andrew F.} and Houssen, {Wael E.} and Shirran, {Sally L.} and Fuszard, {Matthew A.} and Smellie, {Iain A.} and Botting, {Catherine H.} and Smith, {Margaret C. M.} and Marcel Jaspars and Naismith, {James H.}",

note = "Supported by a Wellcome Trust Capital Award (086036)",

year = "2013",

month = mar,

day = "18",

doi = "10.1002/cbic.201300037",

language = "English",

volume = "14",

pages = "564--567",

journal = "ChemBioChem",

issn = "1439-4227",

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T1 - An enzymatic route to selenazolines

AU - Koehnke, Jesko

AU - Morawitz, Falk

AU - Bent, Andrew F.

AU - Houssen, Wael E.

AU - Shirran, Sally L.

AU - Fuszard, Matthew A.

AU - Smellie, Iain A.

AU - Botting, Catherine H.

AU - Smith, Margaret C. M.

AU - Jaspars, Marcel

AU - Naismith, James H.

N1 - Supported by a Wellcome Trust Capital Award (086036)

PY - 2013/3/18

Y1 - 2013/3/18

N2 - Ringing the changes: Selenazolines have applications in medicinal chemistry, but their synthesis is challenging. We report a new convenient and less toxic route to these heterocycles that starts from commercially available selenocysteine. The new route depends on a heterocyclase enzyme that creates oxazolines and thiazolines from serines/threonines and cysteines.

AB - Ringing the changes: Selenazolines have applications in medicinal chemistry, but their synthesis is challenging. We report a new convenient and less toxic route to these heterocycles that starts from commercially available selenocysteine. The new route depends on a heterocyclase enzyme that creates oxazolines and thiazolines from serines/threonines and cysteines.

KW - Patellamides

KW - Macrocyclization

KW - Derivatives

KW - Biochemistry

KW - Line

KW - Biosynthesis

KW - Selenazolines

U2 - 10.1002/cbic.201300037

DO - 10.1002/cbic.201300037

M3 - Article

SN - 1439-4227

VL - 14

SP - 564

EP - 567

JO - ChemBioChem

JF - ChemBioChem

IS - 5

ER -

An enzymatic route to selenazolines

Abstract

Keywords

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Exploring the mechanism: Exploring the mechanism and scope of the enzymatic formation of five membered ring

Cite this