Matches in SemOpenAlex for { <https://semopenalex.org/work/W3194654637> ?p ?o ?g. }
- W3194654637 endingPage "22211" @default.
- W3194654637 startingPage "22207" @default.
- W3194654637 abstract "Abstract Peptidyl asparaginyl ligases (PALs) are powerful tools for peptide macrocyclization. Herein, we report that a derivative of Asn, namely N γ ‐hydroxyasparagine or Asn(OH), is an unnatural P1 substrate of PALs. By Asn(OH)‐mediated cyclization, we prepared cyclic peptides as new matrix metalloproteinase 2 (MMP2) inhibitors displaying the hydroxamic acid moiety of Asn(OH) as the key pharmacophore. The most potent cyclic peptide ( K i =2.8±0.5 nM) was built on the hyperstable tetracyclic scaffold of rhesus theta defensin‐1. The Asn(OH) residue in the cyclized peptides can also be readily oxidized to Asp. By this approach, we synthesized several bioactive Asp‐containing cyclic peptides (MCoTI‐II, kB2, SFTI, and integrin‐targeting RGD peptides) that are otherwise difficult targets for PAL‐catalyzed cyclization owing to unfavorable kinetics of the P1‐Asp substrates. This study demonstrates that substrate engineering is a useful strategy to expand the application of PAL ligation in the synthesis of therapeutic cyclic peptides." @default.
- W3194654637 created "2021-08-30" @default.
- W3194654637 creator A5006623035 @default.
- W3194654637 creator A5008199212 @default.
- W3194654637 creator A5011537784 @default.
- W3194654637 creator A5031590221 @default.
- W3194654637 creator A5034479823 @default.
- W3194654637 creator A5036775735 @default.
- W3194654637 creator A5043274463 @default.
- W3194654637 creator A5058571368 @default.
- W3194654637 creator A5059422020 @default.
- W3194654637 creator A5060129986 @default.
- W3194654637 creator A5078993279 @default.
- W3194654637 date "2021-09-09" @default.
- W3194654637 modified "2023-10-14" @default.
- W3194654637 title "<i>N</i><sup>γ</sup>‐Hydroxyasparagine: A Multifunctional Unnatural Amino Acid That is a Good P1 Substrate of Asparaginyl Peptide Ligases" @default.
- W3194654637 cites W1555403344 @default.
- W3194654637 cites W1594989615 @default.
- W3194654637 cites W1607041879 @default.
- W3194654637 cites W1699671485 @default.
- W3194654637 cites W1794050985 @default.
- W3194654637 cites W1817886125 @default.
- W3194654637 cites W1970012070 @default.
- W3194654637 cites W1979833416 @default.
- W3194654637 cites W1992450378 @default.
- W3194654637 cites W1992521773 @default.
- W3194654637 cites W2010972861 @default.
- W3194654637 cites W2027067039 @default.
- W3194654637 cites W2028277934 @default.
- W3194654637 cites W2038204573 @default.
- W3194654637 cites W2041755933 @default.
- W3194654637 cites W2048797519 @default.
- W3194654637 cites W2049989028 @default.
- W3194654637 cites W2051343450 @default.
- W3194654637 cites W2051437643 @default.
- W3194654637 cites W2072103796 @default.
- W3194654637 cites W2072186058 @default.
- W3194654637 cites W2107177621 @default.
- W3194654637 cites W2108175440 @default.
- W3194654637 cites W2109954853 @default.
- W3194654637 cites W2118185304 @default.
- W3194654637 cites W2128855986 @default.
- W3194654637 cites W2136544846 @default.
- W3194654637 cites W2141779177 @default.
- W3194654637 cites W2161513926 @default.
- W3194654637 cites W2162570875 @default.
- W3194654637 cites W2212250794 @default.
- W3194654637 cites W2267190811 @default.
- W3194654637 cites W2333646594 @default.
- W3194654637 cites W2397734123 @default.
- W3194654637 cites W2519150878 @default.
- W3194654637 cites W2522742593 @default.
- W3194654637 cites W2614400304 @default.
- W3194654637 cites W2724823461 @default.
- W3194654637 cites W2787400035 @default.
- W3194654637 cites W2788197842 @default.
- W3194654637 cites W2792158771 @default.
- W3194654637 cites W2795470773 @default.
- W3194654637 cites W2912930263 @default.
- W3194654637 cites W2913199740 @default.
- W3194654637 cites W2946803285 @default.
- W3194654637 cites W2950244355 @default.
- W3194654637 cites W2953616122 @default.
- W3194654637 cites W2963311769 @default.
- W3194654637 cites W2978834401 @default.
- W3194654637 cites W2988747529 @default.
- W3194654637 cites W3006690501 @default.
- W3194654637 cites W3013178722 @default.
- W3194654637 cites W3042367672 @default.
- W3194654637 cites W3045239092 @default.
- W3194654637 cites W3153722616 @default.
- W3194654637 cites W3169584208 @default.
- W3194654637 cites W4240984668 @default.
- W3194654637 cites W4243577692 @default.
- W3194654637 cites W4251221067 @default.
- W3194654637 doi "https://doi.org/10.1002/anie.202108125" @default.
- W3194654637 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/34396662" @default.
- W3194654637 hasPublicationYear "2021" @default.
- W3194654637 type Work @default.
- W3194654637 sameAs 3194654637 @default.
- W3194654637 citedByCount "4" @default.
- W3194654637 countsByYear W31946546372021 @default.
- W3194654637 countsByYear W31946546372022 @default.
- W3194654637 countsByYear W31946546372023 @default.
- W3194654637 crossrefType "journal-article" @default.
- W3194654637 hasAuthorship W3194654637A5006623035 @default.
- W3194654637 hasAuthorship W3194654637A5008199212 @default.
- W3194654637 hasAuthorship W3194654637A5011537784 @default.
- W3194654637 hasAuthorship W3194654637A5031590221 @default.
- W3194654637 hasAuthorship W3194654637A5034479823 @default.
- W3194654637 hasAuthorship W3194654637A5036775735 @default.
- W3194654637 hasAuthorship W3194654637A5043274463 @default.
- W3194654637 hasAuthorship W3194654637A5058571368 @default.
- W3194654637 hasAuthorship W3194654637A5059422020 @default.
- W3194654637 hasAuthorship W3194654637A5060129986 @default.
- W3194654637 hasAuthorship W3194654637A5078993279 @default.
- W3194654637 hasConcept C124790011 @default.
- W3194654637 hasConcept C168831097 @default.