专利号:WO-2016037298-A1 优先权日:2014-09-11 标题 :Method for the enantioselective synthesis of 2(s)-amino-6-boronohexanoic acid (abh) and purification thereof 发明人:PREITE MARCELO DANIEL; MANRIQUEZ MUJICA JUAN MANUEL; CORREA VARGAS JORDAN MAURICIO; ITURRIAGA AGUERA RODRIGO MANUEL; CASANELLO TOLEDO PAOLA CECILIA; KRAUSE LEYTON BERNARDO JAVIER 权利人:UNIV PONTIFICIA CATOLICA CHILE 摘要:The invention relates to a method for the enantioselective synthesis and purification of 2(S)-amino-6-boronohexanoic acid (ABH) and the preparation of the corresponding synthetic intermediates. The method comprises the preparation of ABH from BPB-Ni-Gly, which is treated with a strong base in a suitable solvent, and is made to react with 2-(4-lower bromoalkyl)benzo[d] [1,3,2]dioxaborol, where the lower alkyl is an alkyl with between 1 and 6 carbon atoms, preferably 2-(4- bromo-butyl)benzo[d][1,3,2]dioxaborol, while stirring, in a nitrogen atmosphere and with a cryogenic bath at a low temperature (-50°C), in order to then permit same to reach ambient temperature, removing the cryogenic bath, before neutralising in aqueous medium with a weak organic acid, and extracting with dichloromethane, drying the resulting organic extract which is subsequently filtered and vacuum evaporated. The resulting alkylated complex is dissolved in a C1-C5 alcohol, adding a hydrochloric acid, refluxing in a nitrogen atmosphere, and is subsequently cooled to ambient temperature, and concentrated in order to achieve the precipitation of (S)-2-[N-(N'- benzylprolyl) amino]benzophenone (BPB), as the hydrochloride salt, filtering and extracting with dichloromethane, and after dissolving the aqueous phase of the filtrate in water, it is treated with ammonia concentrated to pH 9, and once again extracted with dichloromethane, the ammoniacal aqueous phase being vacuum evaporated until dry, in order to produce crude ABH, as the ammonium salt, which is subsequently purified by means of ion-exchange chromatography. The invention also relates to a method for preparing the Gly-Ni-BPB complex, 2-(4- bromo-butyl)benzo[d][1,3,2]dioxaborol, which is used as an alkylating agent in the form of a borate side chain, and (S)-N- benzylproline (BP).
专利号:US-2006183888-A1 优先权日:2004-08-13 标 题:Pyrrolysine synthesis and modification 发明人:CHAN MICHAEL K; KRZYCKI JOSEPH A 权利人:CHAN MICHAEL K; KRZYCKI JOSEPH A 摘要:Synthetic L-pyrrolysine of formula I, and derivatives thereof, chemical methods of preparing these amino acids and derivatives, and methods of derivatizing these amino acids after incorporation into a peptide or protein. n nAlso provided are derivatives and methods of preparing derivatives, including addition of substituents at any substitutable position; modifications to the lysine alkyl chain; modifications of the pyrroline ring. Also provided are methods of adding labels to the pyrrolysine or derivative thereof.
专利号:WO-2018178397-A1 优先权日:2017-03-30 标题 :N-alkylated amino acids and oligopeptides, uses thereof and methods for providing them. 发明人:BARTA KATALIN; YAN TAO; FERINGA BERNARD LUCAS 权利人:UNIV GRONINGEN 摘要:The invention relates to the synthesis of amphiphilic amino acid derivatives, in particular to a method for the N-alkylation of an unprotected amino acid or the N-terminus of an oligopeptide substrate, comprising reacting said unprotected amino acid or oligopeptide substrate with an alcohol, e.g. a fatty alcohol, in the presence of a homogeneous transition metal catalyst.
专利号:CN-104098650-B 优先权日:2013-04-15 标题 :The synthesis and application of the intermediate of Atosiban
专利号:CN-102241674-A 优先权日:2010-05-12 标题 :Synthesis and Antitumor Activity Evaluation of 1,1-Dimethyl-β-carboline-3-formyl Amino Acid Benzyl Ester