http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-986904-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_c7ad58d3c0b071069a8ee0cb8c8ba2e8 |
| classificationCPCAdditional | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/Y02P20-55 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07K1-02 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07K1-06 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07K1-10 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C237-00 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07C237-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07K1-10 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07K1-06 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07K1-02 |
| filingDate | 1962-04-27-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1965-03-24-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-986904-A |
| titleOfInvention | Process for the production of peptides |
| abstract | Peptides are prepared by condensing an amino acid or a functional derivative thereof with a b -dicarbonyl compound (the atom between the carbonyl groups being carbon), converting the carboxyl group of the product into a peptide linkage, and subjecting the product to mild acid treatment to remove the N-protecting group derived from the b -dicarbonyl compound. The amino acid may be used in the form of a salt, ester or amide, or it may itself be a peptide. The b -dicarbonyl compound may be a b -diketone, b -ketoaldehyde, b -ketoester or a b -ketoacid amide. The intermediate condensation product is an imino compound, a carbonyl oxygen being replaced by the amino acid residue, or the corresponding tautomeric enamine. In examples, (1) glycine and benzoylacetone in alcoholic KOH give the K salt of the condensation product, which is reacted with chloroacetonitrile gives the corresponding cyanomethyl ester; this is condensed with glycine ethyl ester to give N-protected glycyl-glycine which is then hydrolysed to glycyl-glycine; (2) glycine and cyclopentanone 2-carboxylic acid ethyl ester similarly give glycyl-glycine ethyl ester hydrochloride, subsequently hydrolysed to glycylglycine; (3) potassium glycine protected by benzoylacetone is reacted with glycine ethyl ester hydrochloride and dicyclohexyl-carbodiimide to produce glycyl-glycine ethyl ester protected by benzoylacetone, which is hydrolysed in two steps to glycyl-glycine; (4) similar to (3), with cyclopentan-2-one-1-carboxylic acid ethyl ester as protecting agent; 5) DL-alanine K salt protected by cyclopentan-2-one-1-carboxylic acid ethyl ester is reacted with chloroacetonitrile to give the corresponding cyanomethyl ester of the protected alanine; reaction with glycine ethyl ester gives the protected alanyl-glycine ester, which is hydrolysed to the K salt and again reacted with chloroacetonitrile and then with glycine ethyl ester; subsequent hydrolysis of the protected tripeptide gives DL-alanyl-glycyl-glycine; (6) L-alanyl-glycine is obtained similarly. Protected amino-acids and derivatives are listed and characterized. |
| isCitedBy | http://rdf.ncbi.nlm.nih.gov/pubchem/patent/JP-2013530948-A http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-9725420-B2 http://rdf.ncbi.nlm.nih.gov/pubchem/patent/EP-2571857-B1 http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-9447052-B2 |
| priorityDate | 1961-04-27-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 57.