80994-59-8

Usage

Uses

Used in Cancer Therapy:
10B-enriched L-4-boronophenylalanine, GMPBPA is used as a therapeutic agent for boron neutron capture therapy (BNCT) for the treatment of cancer. It is employed to selectively deliver boron-10 to tumor cells, where it can react with thermal neutrons to produce lethal alpha particles and lithium nuclei. This targeted approach selectively damages the tumor cells while sparing nearby healthy tissue, making it a promising treatment option for various types of cancer.
Used in Targeted Radiation Therapy:
In the field of targeted radiation therapy, 10B-enriched L-4-boronophenylalanine, GMPBPA is used as a boron carrier for BNCT. Its ability to selectively deliver boron-10 to tumor cells allows for the precise targeting of cancerous tissues, minimizing damage to surrounding healthy cells and reducing the side effects associated with traditional radiation therapy.
Used in Cancer Research:
10B-enriched L-4-boronophenylalanine, GMPBPA is also used in cancer research to study the mechanisms of BNCT and to develop new strategies for the selective delivery of boron-10 to tumor cells. This research aims to improve the efficacy and safety of BNCT, as well as to expand its applicability to a broader range of cancer types.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 10B-enriched L-4-boronophenylalanine, GMPBPA is used in the development of new drugs and therapies for cancer treatment. Its unique properties as a boron carrier for BNCT make it a valuable component in the creation of novel cancer treatments that can offer improved outcomes and reduced side effects for patients.
Overall, 10B-enriched L-4-boronophenylalanine, GMPBPA, is a versatile and promising compound in the field of cancer therapy, with applications in targeted radiation therapy, cancer research, and pharmaceutical development. Its ability to selectively deliver boron-10 to tumor cells and its potential to improve the efficacy and safety of BNCT make it a valuable asset in the ongoing fight against cancer.

Upstream product

• 936247-99-3 d5-(2,2-dicarboxy-2-acetamidoethyl)benzeneboronic acid 
• 1043926-52-8 N^α-benzyloxycarbonyl-p-(10B)borono-L-phenylalanine methyl ester 

Relevant academic research and scientific papers

Preparation method of 4-(borono-10B)-L-phenylalanine

The invention discloses a preparation method of 4-(borono-10B)-L-phenylalanine. The preparation method comprises the following steps: preparing an intermediate, namely N-Boc-4-(borono-10B)-L-phenylalanine by from N-Boc-4-iodo-L-phenylalanine and tri-n-butyl 10-borate; and adding N-Boc-4-(borono-10B)-L-phenylalanine and acetone into a reactor, adding a hydrochloric acid solution, conducting uniformstirring at room temperature, performing heating for a reaction, conducting distilling to remove acetone, reducing the temperature of a residual reaction solution to 10 DEG C or below, regulating a pH value to 5.5-6.5, separating out white solids, filtering out the white solids, conducting pulping and washing with dichloromethane, filtering out the residual solids, and carrying out vacuum dryingto obtain 4-(borono-10B)-L-phenylalanine. By changing a feeding sequence and controlling a reaction rate, the requirement of the reaction on the temperature is lowered, the reaction can be smoothly carried out under a relatively mild low-temperature condition, the consumption of n-butyllithium and borate is reduced, post-reaction treatment is simpler, yield is higher, production cost is greatly saved, and industrialization of the product is made possible.

New synthetic method for [10B]-L-4-boronophenylalanine (LBPA) using [10B]pinacolborane

The present invention relates to a method of synthesizing [^(10)B]LBPA that is a boron compound used in a new anticancer therapeutic technique, Boron neutron capture therapy (BNCT). More specifically, the present invention relates to a synthesis method of [^(10)B]pinacolborane, an intermediate which is important for the synthesis, and a method of synthesizing [^(10)B]LBPA using the same. A method of producing [^(10)B]pinacolborane of the present invention comprises the steps of: (A) replacing [^(10)B]boric acid(^(10)B(OH)_3) with alcohol to convert [^(10)B]boric acid(^(10)B(OH)_3) into [^(10)B]alkyl pinacolboronate (1); and (B) replacing [^(10)B]alkyl pinacolboronate (1) with a reductant to obtain [^(10)B]pinacolborane (2) as in reaction formula 1. The method of producing [^(10)B]pinacolborane according to the present invention has an effect that the method can mass-produce [^(10)B]LBPA at high ^(10)B efficiency by an easy synthesis method, [^(10)B]LBPA being used in a clinical trial of BNCT, the new anticancer therapeutic technique which minimizes side effects on normal cells.COPYRIGHT KIPO 2018

METHOD FOR PREPARING L-BPA

Provided is a method for preparing L-BPA, which includes steps of: reacting N-protected (S)-4-halophenylalanine of Formula I, a boronating agent, Grignard reagent and bis(2-methylaminoethyl)ether to obtain a reaction mixture, wherein the reaction mixture comprises N-protected (S)-4-boronophenylalanine of Formula II and the R2 group represents a protecting group; isolating the N-protected (S)-4-boronophenylalanine from the reaction mixture; and deprotecting the R2 group of the N-protected (S)-4-boronophenylalanine to obtain L-BPA, wherein the L-BPA has a structure of Formula III.

Process for preparing 4-Borono-L-Phenylalanine

Provided is a process for preparing 4-borono-L-phenylalanine, which has steps of: reacting N-protected (S)-4-halophenylalanine of formula (I), a boronating agent and an organolithium to obtain a reaction mixture, wherein the reaction mixture comprises the N-protected (S)-4-boronophenylalanine of formula (II) and the R group represents a protection group; isolating the N-protected (S)-4-boronophenylalanine from the reaction mixture; deprotecting the R group of the N-protected (S)-4-boronophenylalanine to obtain L-BPA.

Compound for preparing 4-(10B)borono-L-phenylalanine

Provided is a compound for preparing 4-(10B)borono-L-phenylalanine, characterized in that the compound is represented by the following formula (I): wherein R group represents a protection group and is selected from the group consisting of: tert-butoxycarbonyl (Boc) group, trityl (Trt) group, 3,5-dimethoxyphenylisopropoxycarbonyl (Ddz) group, 2-(4-Biphenyl)isopropoxycarbonyl (Bpoc) group, and 2-nitrophenylsulfenyl (Nps) group, and the compound has a 10B purity higher than or equal to 98 % and an enantiomeric excess higher than or equal to 99%.

COMPOUND FOR PREPARING 4-(10B)BORONO-L-PHENYLALANINE

Provided is a compound of the following formula (I) for preparing 4-(10B)borono-L-phenylalnine: wherein R group represents a protecting group and is selected from the group consisting of: tert-butoxycarbonyl (Boc) group, trityl (Trt) group, 3,5-dimethoxyphenylisopropoxycarbonyl(Ddz) group, 2-(4-Biphenyl)isopropoxycarbonyl (Bpoc) group, and 2-nitrophenylsulfenyl (Nps) group, and the compound has a 10B purity higher than or equal to 98% and an enantiomeric excess higher than or equal to 99%.

Development of the first and practical method for enantioselective synthesis of 10B-enriched p-borono-l-phenylalanine

At present p-(10B)borono-l-phenylalanine (l-10Bpa) is used clinically as an excellent 10B carrier for BNCT; however, its enantioselective synthesis has not been reported yet. The present Letter describes the first and prac

Compositions, methods of preparing amino acids, and nuclear magnetic resonance spectroscopy

The present invention relates to amino acids, complexes, and compounds comprising deuterium and tritium isotopes preferably alpha deuterated amino acids, polypeptides, antibodies, derivatives and saccharide-amino acid complexes and conjugates. In some embodiments, the invention relates to methods of using compounds comprising deuterium for imaging biochemical concentrations and distributions in mammalian tissues using nuclear magnetic resonance spectroscopy. In some embodiments, the invention relates to the used of said amino acids derivatives and complexes in boron neutron capture therapy. In some embodiments, the present invention relates to the preparation of amino acids, polypeptides, antibodies, derivatives and saccharide complexes/conjugates comprising heavy hydrogen isotopes. In some embodiments, the invention relates to racemizing amino acids starting from compositions of any optical purity. In further embodiments, the invention relates to the preparation of amino acids and their N-acyl counterparts with deuterium incorporated at the alpha carbon.