A facile synthesis of cysteine-based diketopiperazine from thiol-protected precursor

A facile synthesis of cysteine-based diketopiperazine from thiol-protected precursor

l-Cysteine is one of the most promising biomass-based building blocks with great potential applications. Herein, we report a versatile synthetic route to produce cysteine-based 2,5-diketopiperazine (DKP) with good yield from the thiol-ene click reaction of l-cysteine and commercially available acryl...

Full description

Bibliographic Details
Main Authors: Di Zhang, Wayne Wang
Format: Article
Language:English
Published: The Royal Society 2018-01-01
Series:Royal Society Open Science
Subjects:
l-cysteine
diketopiperazines
diastereomer
chiroptical
Online Access:https://royalsocietypublishing.org/doi/pdf/10.1098/rsos.180272
id doaj-68c4681608a14fc9b202409b94bf749c
record_format Article
spelling doaj-68c4681608a14fc9b202409b94bf749c2020-11-25T04:06:37ZengThe Royal SocietyRoyal Society Open Science2054-57032018-01-015610.1098/rsos.180272180272A facile synthesis of cysteine-based diketopiperazine from thiol-protected precursorDi ZhangWayne Wangl-Cysteine is one of the most promising biomass-based building blocks with great potential applications. Herein, we report a versatile synthetic route to produce cysteine-based 2,5-diketopiperazine (DKP) with good yield from the thiol-ene click reaction of l-cysteine and commercially available acrylates, followed by dimerization of the amino acid intermediates. The achieved DKP diastereomers were successfully separated and fully characterized by spectroscopic methods. Moreover, the chiroptical property of DKP in the presence of various metal ions was investigated by circular dichroism spectroscopy. The potential application of the optically active cysteine-based DKP as a chiral probe for detection of silver ion in water has been demonstrated.https://royalsocietypublishing.org/doi/pdf/10.1098/rsos.180272l-cysteinediketopiperazinesdiastereomerchiroptical
collection DOAJ
language English
format Article
sources DOAJ
author Di Zhang
Wayne Wang
spellingShingle Di Zhang
Wayne Wang
A facile synthesis of cysteine-based diketopiperazine from thiol-protected precursor
Royal Society Open Science
l-cysteine
diketopiperazines
diastereomer
chiroptical
author_facet Di Zhang
Wayne Wang
author_sort Di Zhang
title A facile synthesis of cysteine-based diketopiperazine from thiol-protected precursor
title_short A facile synthesis of cysteine-based diketopiperazine from thiol-protected precursor
title_full A facile synthesis of cysteine-based diketopiperazine from thiol-protected precursor
title_fullStr A facile synthesis of cysteine-based diketopiperazine from thiol-protected precursor
title_full_unstemmed A facile synthesis of cysteine-based diketopiperazine from thiol-protected precursor
title_sort facile synthesis of cysteine-based diketopiperazine from thiol-protected precursor
publisher The Royal Society
series Royal Society Open Science
issn 2054-5703
publishDate 2018-01-01
description l-Cysteine is one of the most promising biomass-based building blocks with great potential applications. Herein, we report a versatile synthetic route to produce cysteine-based 2,5-diketopiperazine (DKP) with good yield from the thiol-ene click reaction of l-cysteine and commercially available acrylates, followed by dimerization of the amino acid intermediates. The achieved DKP diastereomers were successfully separated and fully characterized by spectroscopic methods. Moreover, the chiroptical property of DKP in the presence of various metal ions was investigated by circular dichroism spectroscopy. The potential application of the optically active cysteine-based DKP as a chiral probe for detection of silver ion in water has been demonstrated.
topic l-cysteine
diketopiperazines
diastereomer
chiroptical
url https://royalsocietypublishing.org/doi/pdf/10.1098/rsos.180272
work_keys_str_mv AT dizhang afacilesynthesisofcysteinebaseddiketopiperazinefromthiolprotectedprecursor
AT waynewang afacilesynthesisofcysteinebaseddiketopiperazinefromthiolprotectedprecursor
AT dizhang facilesynthesisofcysteinebaseddiketopiperazinefromthiolprotectedprecursor
AT waynewang facilesynthesisofcysteinebaseddiketopiperazinefromthiolprotectedprecursor
_version_ 1724431335315996672

Similar Items