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Selective lysine modification of native peptides via aza-Michael addition.
| Content Provider | Semantic Scholar |
|---|---|
| Author | Chen, Hongli Huang, Rong Li, Zhihong Chen, Jiakang Zhan, Yuexiong Jiang, Biao |
| Copyright Year | 2017 |
| Abstract | A series of vinylsulfonamides were synthesized and screened for site-selective modification of the ε-amino group of lysine-bearing free α-amine residues. N-Methyl-N-phenylethenesulfonamide has emerged as an applicable reagent and has been developed for efficient and highly selective modification of the lysine residue of native peptides in the presence of a free N-terminus via aza-Michael addition. We demonstrated that functional N-phenylvinylsulfonamide derivatives with a fluorescent moiety or drug could also be conjugated to the lysine residue of octreotide and insulin with high specificity, without modifying the N-terminus. Our method provides a promising strategy for site-selective lysine functionalization in native peptides with a free N-terminus. |
| Starting Page | 7339 |
| Ending Page | 7345 |
| Page Count | 7 |
| File Format | PDF HTM / HTML |
| DOI | 10.1039/c7ob01866e |
| PubMed reference number | 28853470 |
| Journal | Medline |
| Volume Number | 15 |
| Issue Number | 35 |
| Alternate Webpage(s) | https://pubs.rsc.org/en/content/articlepdf/2017/ob/c7ob01866e |
| Alternate Webpage(s) | http://pubs.rsc.org/en/content/articlepdf/2017/ob/c7ob01866e |
| Alternate Webpage(s) | http://www.rsc.org/suppdata/c7/ob/c7ob01866e/c7ob01866e1.pdf |
| Alternate Webpage(s) | https://doi.org/10.1039/c7ob01866e |
| Journal | Organic & biomolecular chemistry |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
