Ligase-controlled cyclo-oligomerization of peptides
A biomimetic one-step ligase-catalyzed cyclo-oligomerization mediated by butelase 1, an Asn/Asp-specific ligase, is introduced that is time-, concentration-, length-, and sequence-dependent. This reaction yields cyclic mono-, di-, tri-, and tetramers from peptide precursors containing 3-15 amino aci...
| Main Authors: | , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2020
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| Online Access: | https://hdl.handle.net/10356/143886 |
| _version_ | 1811679565169295360 |
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| author | Hemu, Xinya Zhang, Xiaohong Tam, James P. |
| author2 | School of Biological Sciences |
| author_facet | School of Biological Sciences Hemu, Xinya Zhang, Xiaohong Tam, James P. |
| author_sort | Hemu, Xinya |
| collection | NTU |
| description | A biomimetic one-step ligase-catalyzed cyclo-oligomerization mediated by butelase 1, an Asn/Asp-specific ligase, is introduced that is time-, concentration-, length-, and sequence-dependent. This reaction yields cyclic mono-, di-, tri-, and tetramers from peptide precursors containing 3-15 amino acids ended with Asn and a His-Val tail. The cyclomonomers were favored when the peptide lengths were >9 amino acids. A turn-forming Pro residue at the P2 position favored the formation of higher-order cyclo-oligomers. |
| first_indexed | 2024-10-01T03:11:10Z |
| format | Journal Article |
| id | ntu-10356/143886 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T03:11:10Z |
| publishDate | 2020 |
| record_format | dspace |
| spelling | ntu-10356/1438862023-02-28T17:07:03Z Ligase-controlled cyclo-oligomerization of peptides Hemu, Xinya Zhang, Xiaohong Tam, James P. School of Biological Sciences Science::Biological sciences Peptides And Proteins Bacteria A biomimetic one-step ligase-catalyzed cyclo-oligomerization mediated by butelase 1, an Asn/Asp-specific ligase, is introduced that is time-, concentration-, length-, and sequence-dependent. This reaction yields cyclic mono-, di-, tri-, and tetramers from peptide precursors containing 3-15 amino acids ended with Asn and a His-Val tail. The cyclomonomers were favored when the peptide lengths were >9 amino acids. A turn-forming Pro residue at the P2 position favored the formation of higher-order cyclo-oligomers. Ministry of Education (MOE) Accepted version We thank National University Hospital of Singapore for providing the drug-resistant bacteria strains for the research purpose. This research was supported by Academic Research Grant Tier 3 (MOE2016-T3-1-003) from Singapore Minister of Education (MOE). 2020-09-29T07:47:55Z 2020-09-29T07:47:55Z 2019 Journal Article Hemu, X., Zhang, X., & Tam, J. P. (2019). Ligase-Controlled Cyclo-oligomerization of Peptides. Organic Letters, 21(7), 2029–2032. doi:10.1021/acs.orglett.9b00151 1523-7060 https://hdl.handle.net/10356/143886 10.1021/acs.orglett.9b00151 30763108 7 21 2029 2032 en Organic letters This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.9b00151 application/pdf |
| spellingShingle | Science::Biological sciences Peptides And Proteins Bacteria Hemu, Xinya Zhang, Xiaohong Tam, James P. Ligase-controlled cyclo-oligomerization of peptides |
| title | Ligase-controlled cyclo-oligomerization of peptides |
| title_full | Ligase-controlled cyclo-oligomerization of peptides |
| title_fullStr | Ligase-controlled cyclo-oligomerization of peptides |
| title_full_unstemmed | Ligase-controlled cyclo-oligomerization of peptides |
| title_short | Ligase-controlled cyclo-oligomerization of peptides |
| title_sort | ligase controlled cyclo oligomerization of peptides |
| topic | Science::Biological sciences Peptides And Proteins Bacteria |
| url | https://hdl.handle.net/10356/143886 |
| work_keys_str_mv | AT hemuxinya ligasecontrolledcyclooligomerizationofpeptides AT zhangxiaohong ligasecontrolledcyclooligomerizationofpeptides AT tamjamesp ligasecontrolledcyclooligomerizationofpeptides |