http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-2015291699-A1
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_2a819eda0adf22936a52362eeebb9fb4 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D311-92 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07K16-32 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D405-12 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D209-12 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D498-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D495-04 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07K16-32 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D495-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D498-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D405-12 |
| filingDate | 2013-11-15-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| inventor | http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_60057bce44c41783722d10a3c6eb7207 http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_aba1bb2c45103e832b461e585f818113 http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_c6e5b2e5a18e26457c74d2994bf2a677 |
| publicationDate | 2015-10-15-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | US-2015291699-A1 |
| titleOfInvention | Pictet-spengler ligation for protein chemical modification |
| abstract | Aldehyde- and ketone-functionalized proteins are promising new substrates for the development of chemically modified biotherapeutics and protein-based materials. Their reactive carbonyl groups are typically conjugated with a-effect nucleophiles, such as substituted hydrazines and alkoxyamines, to generate hydrazones and oximes, respectively. However, the resulting C═N linkages are susceptible to hydrolysis under physiologically relevant conditions, which limits their utility in biological systems. Here we introduce a Pictet-Spengler ligation that is based on the classic Pictet-Spengler reaction of aldehydes and tryptamine nucleophiles. The ligation exploits the bioorthogonal reaction of aldehydes and alkoxyamines to form an intermediate oxyiminium ion; this intermediate undergoes intramolecular C—C bond formation with an indole nucleophile to form an oxacarboline product that is hydrolytically stable. The reaction was utilized for site-specific chemical modification of glyoxal- and formylglycine-functionalized proteins, including an aldehyde-tagged variant of the therapeutic monoclonal antibody Herceptin. In conjunction with techniques for site-specific introduction of aldehydes into proteins, the Pictet-Spengler ligation offers a new means to generate stable bioconjugates for medical and materials applications. |
| isCitedBy | http://rdf.ncbi.nlm.nih.gov/pubchem/patent/EP-3373009-A1 http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-10660966-B2 http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-11389538-B2 http://rdf.ncbi.nlm.nih.gov/pubchem/patent/WO-2022251357-A1 http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-2017360943-A1 |
| priorityDate | 2012-11-16-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
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