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...
| Main Author: | |
|---|---|
| Format: | Book Section |
| Language: | English |
| Published: |
Institute of Graduate Studies
2017
|
| Subjects: | |
| Online Access: | https://ir.uitm.edu.my/id/eprint/18952/ |
| _version_ | 1848804649139699712 |
|---|---|
| author | Kamaruddin, Nurulhuda |
| author_facet | Kamaruddin, Nurulhuda |
| author_sort | Kamaruddin, Nurulhuda |
| building | UiTM Institutional Repository |
| collection | Online Access |
| 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.. |
| first_indexed | 2025-11-14T21:58:29Z |
| format | Book Section |
| id | uitm-18952 |
| institution | Universiti Teknologi MARA |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T21:58:29Z |
| publishDate | 2017 |
| publisher | Institute of Graduate Studies |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | uitm-189522018-02-22T01:37:35Z https://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 https://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. (2017) In: The Doctoral Research Abstracts. IGS Biannual Publication, 12 (12). Institute of Graduate Studies, Shah Alam. |
| spellingShingle | Analytical chemistry Kamaruddin, Nurulhuda Chemical studies towards the synthesis of janolusimide, a marine neurotoxin from janolus cristatus / Nurulhuda Kamaruddin |
| title | 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_short | 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 |
| topic | Analytical chemistry |
| url | https://ir.uitm.edu.my/id/eprint/18952/ |