Chemical studies towards the synthesis of janolusimide, a marine neurotoxin from janolus cristatus / Nurulhuda Kamaruddin

Chemical studies towards the synthesis of janolusimide, a marine neurotoxin from janolus cristatus / Nurulhuda Kamaruddin

Janolusimide 19 was chosen to be the synthetic target molecule due to having a unique tripeptide structure besides showing a neurotoxin activity. Our synthetic approach towards the synthesis of janolusimide involved the construction of a core lactam system derived from L-valine using EDC.HCl fol...

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Main Author: Kamaruddin, Nurulhuda
Format: Book Section
Language:English
Published: Institute of Graduate Studies 2017
Subjects:
Analytical chemistry
Online Access:http://ir.uitm.edu.my/id/eprint/18952/
http://ir.uitm.edu.my/id/eprint/18952/1/ABS_NURULHUDA%20KAMARUDDIN%20TDRA%20VOL%2012%20IGS%2017.pdf
id uitm-18952
recordtype eprints
spelling uitm-189522018-02-22T01:37:35Z http://ir.uitm.edu.my/id/eprint/18952/ Chemical studies towards the synthesis of janolusimide, a marine neurotoxin from janolus cristatus / Nurulhuda Kamaruddin Kamaruddin, Nurulhuda Analytical chemistry Janolusimide 19 was chosen to be the synthetic target molecule due to having a unique tripeptide structure besides showing a neurotoxin activity. Our synthetic approach towards the synthesis of janolusimide involved the construction of a core lactam system derived from L-valine using EDC.HCl followed by dimethylation using four different conditions. Dimethylation at C-3 position of 133 affords (5S)-3,3- dimethyl-5-isopropylpyrrolidine-2,4-dione 26 in 72% yield using TBAF as a phase transfer catalyst. In this dimethylation step, a characteristic of ambident anion also can be observed. Multiple positions of alkylation had occurred due to enolate’s ambident character of which C,O-alkylated and O-alkylated side products were observed. While the effort to synthesize the dipeptide chain was carried out using aldol reaction, N-alkylation of 26 and N-acylation of a template, 2-pyrrolidinone 139 and lactam 26 with several electrophiles. Four general protocols (Method A-D) to N-acylate 2-pyrrolidinone and lactam 26 were examined.. Institute of Graduate Studies 2017 Book Section PeerReviewed text en http://ir.uitm.edu.my/id/eprint/18952/1/ABS_NURULHUDA%20KAMARUDDIN%20TDRA%20VOL%2012%20IGS%2017.pdf Kamaruddin, Nurulhuda (2017) Chemical studies towards the synthesis of janolusimide, a marine neurotoxin from janolus cristatus / Nurulhuda Kamaruddin. In: The Doctoral Research Abstracts. IGS Biannual Publication, 12 (12). Institute of Graduate Studies, Shah Alam.
repository_type Digital Repository
institution_category Local University
institution Universiti Teknologi MARA
building UiTM Institutional Repository
collection Online Access
language English
topic Analytical chemistry
spellingShingle Analytical chemistry
Kamaruddin, Nurulhuda
Chemical studies towards the synthesis of janolusimide, a marine neurotoxin from janolus cristatus / Nurulhuda Kamaruddin
description Janolusimide 19 was chosen to be the synthetic target molecule due to having a unique tripeptide structure besides showing a neurotoxin activity. Our synthetic approach towards the synthesis of janolusimide involved the construction of a core lactam system derived from L-valine using EDC.HCl followed by dimethylation using four different conditions. Dimethylation at C-3 position of 133 affords (5S)-3,3- dimethyl-5-isopropylpyrrolidine-2,4-dione 26 in 72% yield using TBAF as a phase transfer catalyst. In this dimethylation step, a characteristic of ambident anion also can be observed. Multiple positions of alkylation had occurred due to enolate’s ambident character of which C,O-alkylated and O-alkylated side products were observed. While the effort to synthesize the dipeptide chain was carried out using aldol reaction, N-alkylation of 26 and N-acylation of a template, 2-pyrrolidinone 139 and lactam 26 with several electrophiles. Four general protocols (Method A-D) to N-acylate 2-pyrrolidinone and lactam 26 were examined..
format Book Section
author Kamaruddin, Nurulhuda
author_facet Kamaruddin, Nurulhuda
author_sort Kamaruddin, Nurulhuda
title Chemical studies towards the synthesis of janolusimide, a marine neurotoxin from janolus cristatus / Nurulhuda Kamaruddin
title_short Chemical studies towards the synthesis of janolusimide, a marine neurotoxin from janolus cristatus / Nurulhuda Kamaruddin
title_full Chemical studies towards the synthesis of janolusimide, a marine neurotoxin from janolus cristatus / Nurulhuda Kamaruddin
title_fullStr Chemical studies towards the synthesis of janolusimide, a marine neurotoxin from janolus cristatus / Nurulhuda Kamaruddin
title_full_unstemmed Chemical studies towards the synthesis of janolusimide, a marine neurotoxin from janolus cristatus / Nurulhuda Kamaruddin
title_sort chemical studies towards the synthesis of janolusimide, a marine neurotoxin from janolus cristatus / nurulhuda kamaruddin
publisher Institute of Graduate Studies
publishDate 2017
url http://ir.uitm.edu.my/id/eprint/18952/
http://ir.uitm.edu.my/id/eprint/18952/1/ABS_NURULHUDA%20KAMARUDDIN%20TDRA%20VOL%2012%20IGS%2017.pdf
first_indexed 2023-09-18T23:01:32Z
last_indexed 2023-09-18T23:01:32Z
_version_ 1777418206352244736

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