Concept and synthetic approach for a kilogram scale synthesis of octa-d-arginine amide nonahydrochloride salt

Autor:	John C. Tolle, G. Love, D. Zhou, C. L. Becker, V. Kishore, J. C. Califano, K. Gernhardt, A. Uribe, J. J. Napier, J. L. Chang
Rok vydání:	2005
Předmět:	chemistry.chemical_classification Arginine Stereochemistry Organic Chemistry Salt (chemistry) Ornithine Biochemistry D-Arginine chemistry.chemical_compound Membrane chemistry Peptide transport Amide Drug Discovery Molecule
Zdroj:	Tetrahedron. 61:8821-8829
ISSN:	0040-4020
DOI:	10.1016/j.tet.2005.07.037
Popis:	Oligomers of arginine, such as octa- d -arginine amide, are excellent transporters for active drugs through cell membranes and tissue. The synthesis of octa- d -arginine amide, as the nonahydrochloride salt, was approached via a solution phase synthetic route involving the preparation of an octa- d -ornithine intermediate, which was then converted into the desired octa- d -arginine compound through a guanidinylation step. The multi-step synthesis was carried out at pilot scale, resulting in the preparation of 700 g of the target molecule. No chromatographic purification was needed at any step of the process.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::c607437e538e75455353f6855f8b91d5 https://doi.org/10.1016/j.tet.2005.07.037 Zobrazit plný text záznamu Full Text from ScienceDirect