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76410-58-7,MFCD01075172
Catalog No.:AA005Y1D

76410-58-7 | 4-Borono-L-phenylalanine

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  • Technical Information
  • Properties
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Technical Information
Catalog Number:
AA005Y1D
Chemical Name:
4-Borono-L-phenylalanine
CAS Number:
76410-58-7
Molecular Formula:
C9H12BNO4
Molecular Weight:
209.0069
MDL Number:
MFCD01075172
SMILES:
OC(=O)[C@H](Cc1ccc(cc1)B(O)O)N
Properties
Properties
 
BP:
449.3 °C at 760 mmHg  
Form:
Solid  
MP:
285-293℃ (dec.)  
Storage:
Inert atmosphere;2-8℃;  

Computed Properties
 
Complexity:
216  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Heavy Atom Count:
15  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
4  
Rotatable Bond Count:
4  

Literature

Title: Macro- and microdistributions of boron drug for boron neutron capture therapy in an animal model.

Journal: Anticancer research 20120701

Title: Boron neutron capture therapy in the treatment of locally recurred head-and-neck cancer: final analysis of a phase I/II trial.

Journal: International journal of radiation oncology, biology, physics 20120101

Title: Tumor blood vessel 'normalization' improves the therapeutic efficacy of boron neutron capture therapy (BNCT) in experimental oral cancer.

Journal: Radiation research 20120101

Title: Evaluation of BPA uptake in clear cell sarcoma (CCS) in vitro and development of an in vivo model of CCS for BNCT studies.

Journal: Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20111201

Title: Boron neutron capture therapy for clear cell sarcoma (CCS): biodistribution study of p-borono-L-phenylalanine in CCS-bearing animal models.

Journal: Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20111201

Title: BPA uptake does not correlate with LAT1 and Ki67 expressions in tumor samples (results of EORTC trial 11001).

Journal: Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20111201

Title: Low dose of gamma irradiation enhanced boronophenylalanine uptake in head and neck carcinoma cells for boron neutron capture therapy.

Journal: Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20111201

Title: Studies for the application of boron neutron capture therapy to the treatment of differentiated thyroid cancer.

Journal: Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20111201

Title: Artificial neural networks to evaluate the boron concentration decreasing profile in blood-BPA samples of BNCT patients.

Journal: Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20111201

Title: Boron Neutron Capture Therapy (BNCT) in an oral precancer model: therapeutic benefits and potential toxicity of a double application of BNCT with a six-week interval.

Journal: Oral oncology 20111101

Title: Boron determination in liver tissue by combining quantitative neutron capture radiography (QNCR) and histological analysis for BNCT treatment planning at the TRIGA Mainz.

Journal: Radiation research 20110901

Title: Induction of multinucleation in oral squamous cell carcinoma tissue with mutated p53 surviving boron neutron capture therapy.

Journal: International journal of radiation biology 20110301

Title: First evaluation of the biologic effectiveness factors of boron neutron capture therapy (BNCT) in a human colon carcinoma cell line.

Journal: International journal of radiation oncology, biology, physics 20110101

Title: 8-Modified-2'-deoxyadenosine analogues induce delayed polymerization arrest during HIV-1 reverse transcription.

Journal: PloS one 20110101

Title: Early effect of boron neutron capture therapy mediated by boronophenylalanine (BPA-BNCT) on mast cells in premalignant tissue and tumors of the hamster cheek pouch.

Journal: Oral oncology 20100501

Title: Metabolism of borono-phenylalanine-fructose complex (BPA-fr) and borocaptate sodium (BSH) in cancer patients--results from EORTC trial 11001.

Journal: Journal of pharmaceutical and biomedical analysis 20100105

Title: Genetic incorporation of unnatural amino acids into proteins in Mycobacterium tuberculosis.

Journal: PloS one 20100101

Title: Boron neutron capture therapy induces apoptosis of glioma cells through Bcl-2/Bax.

Journal: BMC cancer 20100101

Title: Biodistribution of (10)B for Boron Neutron Capture Therapy (BNCT) in a mouse model after injection of sodium mercaptoundecahydro-closo-dodecaborate and l-para-boronophenylalanine.

Journal: Radiation research 20091001

Title: What additional factors beyond state-of-the-art analytical methods are needed for optimal generation and interpretation of biomonitoring data?

Journal: Environmental health perspectives 20091001

Title: EORTC trial 11001: distribution of two 10B-compounds in patients with squamous cell carcinoma of head and neck, a translational research/phase 1 trial.

Journal: Journal of cellular and molecular medicine 20090801

Title: Evolution of proteins with genetically encoded 'chemical warheads'.

Journal: Journal of the American Chemical Society 20090722

Title: Early clinical trial concept for boron neutron capture therapy: a critical assessment of the EORTC trial 11001.

Journal: Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20090701

Title: Suitability of boron carriers for BNCT: accumulation of boron in malignant and normal liver cells after treatment with BPA, BSH and BA.

Journal: Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20090701

Title: Boronophenylalanine uptake in C6 glioma model is dramatically increased by L-DOPA preloading.

Journal: Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20090701

Title: BNCT for skin melanoma in extremities: updated Argentine clinical results.

Journal: Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20090701

Title: Boron neutron capture therapy for newly diagnosed glioblastoma: a pilot study in Tsukuba.

Journal: Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20090701

Title: Boron biodistribution study in colorectal liver metastases patients in Argentina.

Journal: Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20090701

Title: Dose distribution and clinical response of glioblastoma treated with boron neutron capture therapy.

Journal: Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20090701

Title: Boron neutron capture therapy (BNCT) inhibits tumor development from precancerous tissue: an experimental study that supports a potential new application of BNCT.

Journal: Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20090701

Title: Biodistribution of BPA and BSH after single, repeated and simultaneous administrations for neutron-capture therapy of cancer.

Journal: Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20090701

Title: Feasibility of boron neutron capture therapy for malignant spinal tumors.

Journal: Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20090701

Title: Extra-corporeal liver BNCT for the treatment of diffuse metastases: what was learned and what is still to be learned.

Journal: Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20090701

Title: Selective uptake of p-boronophenylalanine by osteosarcoma cells for boron neutron capture therapy.

Journal: Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20090701

Title: Feasibility study on the utilization of boron neutron capture therapy (BNCT) in a rat model of diffuse lung metastases.

Journal: Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20090701

Title: Boron neutron capture therapy for recurrent oral cancer and metastasis of cervical lymph node.

Journal: Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20090701

Title: Biological evaluation of boronated unnatural amino acids as new boron carriers.

Journal: Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20090701

Title: Survival benefit from boron neutron capture therapy for the newly diagnosed glioblastoma patients.

Journal: Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20090701

Title: T2 corrected quantification method of L-p-boronophenylalanine using proton magnetic resonance spectroscopy for boron neutron capture therapy.

Journal: Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20090701

Title: Comparison of BNCT and GdNCT efficacy in treatment of canine cancer.

Journal: Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20090701

Title: Synthesis and evaluation of a novel liposome containing BPA-peptide conjugate for BNCT.

Journal: Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20090701

Title: A cancer research UK pharmacokinetic study of BPA-mannitol in patients with high grade glioma to optimise uptake parameters for clinical trials of BNCT.

Journal: Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20090701

Title: Boron neutron capture therapy at the crossroads: challenges and opportunities.

Journal: Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20090701

Title: Boron neutron capture therapy of EGFR or EGFRvIII positive gliomas using either boronated monoclonal antibodies or epidermal growth factor as molecular targeting agents.

Journal: Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20090701

Title: A simple and rapid method for measurement of (10)B-para-boronophenylalanine in the blood for boron neutron capture therapy using fluorescence spectrophotometry.

Journal: Journal of radiation research 20090701

Title: When studies collide. Rethinking the evidence on BPA.

Journal: Newsweek 20090629

Title: Boron neutron capture therapy for newly diagnosed glioblastoma.

Journal: Radiotherapy and oncology : journal of the European Society for Therapeutic Radiology and Oncology 20090401

Title: L-amino acid transporter-1 and boronophenylalanine-based boron neutron capture therapy of human brain tumors.

Journal: Cancer research 20090301

Title: An international dosimetry exchange for BNCT part II: computational dosimetry normalizations.

Journal: Medical physics 20081201

Title: L-DOPA preloading increases the uptake of borophenylalanine in C6 glioma rat model: a new strategy to improve BNCT efficacy.

Journal: International journal of radiation oncology, biology, physics 20081001

Title: 10B-editing 1H-detection and 19F MRI strategies to optimize boron neutron capture therapy.

Journal: Magnetic resonance imaging 20080901

Title: Functional and histological changes in rat lung after boron neutron capture therapy.

Journal: Radiation research 20080701

Title: Synthesis of C3-symmetric and C4-symmetric amino acid derivatives via Suzuki-Miyaura cross-coupling reaction.

Journal: Amino acids 20080601

Title: [Boron delivery system for neutron capture therapy of cancer].

Journal: [Rinsho ketsueki] The Japanese journal of clinical hematology 20080501

Title: Boron neutron capture therapy for glioblastoma.

Journal: Cancer letters 20080418

Title: Uptake of two 10B-compounds in liver metastases of colorectal adenocarcinoma for extracorporeal irradiation with boron neutron capture therapy (EORTC Trial 11001).

Journal: International journal of cancer 20080301

Title: Effect of neutron capture therapy on the cell cycle of human squamous cell carcinoma cells.

Journal: International journal of radiation biology 20080301

Title: Quantitative subcellular imaging of boron compounds in individual mitotic and interphase human glioblastoma cells with imaging secondary ion mass spectrometry (SIMS).

Journal: Journal of microscopy 20080101

Title: A genetically encoded boronate-containing amino acid.

Journal: Angewandte Chemie (International ed. in English) 20080101

Title: Optimization of boron neutron capture therapy for the treatment of undifferentiated thyroid cancer.

Journal: International journal of radiation oncology, biology, physics 20071115

Title: Effect of Boron Neutron Capture Therapy (BNCT) on normal liver regeneration: towards a novel therapy for liver metastases.

Journal: International journal of radiation biology 20071001

Title: Neuropathological postmortem evaluation of BNCT for GBM.

Journal: Acta neurologica Scandinavica 20070901

Title: Boron neutron capture therapy in cancer: past, present and future.

Journal: Arquivos brasileiros de endocrinologia e metabologia 20070701

Title: Assessment of chemical purity of 10B-enriched p-boronophenylalanine by high-performance liquid chromatography coupled on-line with inductively coupled plasma optical emission spectrometry.

Journal: Analytical and bioanalytical chemistry 20070501

Title: Synthesis and evaluation as MRI probe of the trifluoromethylated p-boronophenylalanine and its alcohol derivative.

Journal: Bioorganic & medicinal chemistry 20070301

Title: Uptake of 4-borono-2-[18F]fluoro-L-phenylalanine in sporadic and neurofibromatosis 2-related schwannoma and meningioma studied with PET.

Journal: European journal of nuclear medicine and molecular imaging 20070101

Title: Synthesis of bis-armed amino acid derivatives via the alkylation of ethyl isocyanoacetate and the Suzuki-Miyaura cross-coupling reaction.

Journal: Amino acids 20070101

Title: Biological evaluation of fluorinated p-boronophenylalanine derivatives as a boron carrier.

Journal: Protein and peptide letters 20070101

Title: An efficient method for the construction of functionalized DNA bearing amino acid groups through cross-coupling reactions of nucleoside triphosphates followed by primer extension or PCR.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20070101

Title: Homogeneous boron targeting of heterogeneous tumors for boron neutron capture therapy (BNCT): chemical analyses in the hamster cheek pouch oral cancer model.

Journal: Archives of oral biology 20061001

Title: First clinical case of boron neutron capture therapy for head and neck malignancies using 18F-BPA PET.

Journal: Head & neck 20060901

Title: Pharmacokinetic study of BSH and BPA in simultaneous use for BNCT.

Journal: Journal of neuro-oncology 20060701

Title: Cross-coupling reactions of unprotected halopurine bases, nucleosides, nucleotides and nucleoside triphosphates with 4-boronophenylalanine in water. Synthesis of (purin-8-yl)- and (purin-6-yl)phenylalanines.

Journal: Organic & biomolecular chemistry 20060607

Title: Depletion of neural precursor cells after local brain irradiation is due to radiation dose to the parenchyma, not the vasculature.

Journal: Radiation research 20060501

Title: Improvement of the tumor-suppressive effect of boron neutron capture therapy for amelanotic melanoma by intratumoral injection of the tyrosinase gene.

Journal: Cancer research 20060401

Title: Capillary electrophoresis-electrospray mass spectrometry and HR-ICP-MS for the detection and quantification of 10B-boronophenylalanine (10B-BPA) used in boron neutron capture therapy.

Journal: Analytical and bioanalytical chemistry 20060201

Title: Effects of boron neutron capture therapy on human oral squamous cell carcinoma in a nude mouse model.

Journal: International journal of radiation biology 20060101

Title: [Boron neutron capture therapy applied to undifferentiated thyroid carcinoma].

Journal: Medicina 20060101

Title: Analysis of 10B antitumoral compounds by means of flow-injection into ESI-MS/MS.

Journal: Journal of mass spectrometry : JMS 20051201

Title: Approach to magnetic neutron capture therapy.

Journal: International journal of radiation oncology, biology, physics 20051101

Title: Noninvasive quantitative in vivo mapping and metabolism of boronophenylalanine (BPA) by nuclear magnetic resonance (NMR) spectroscopy and imaging.

Journal: Radiation research 20051101

Title: Synthesis of the side chain cross-linked tyrosine oligomers dityrosine, trityrosine, and pulcherosine.

Journal: The Journal of organic chemistry 20050902

Title: Optimized 1H MRS and MRSI methods for the in vivo detection of boronophenylalanine.

Journal: Magnetic resonance in medicine 20050501

Title: Synthesis and in vivo biodistribution of BPA-Gd-DTPA complex as a potential MRI contrast carrier for neutron capture therapy.

Journal: Bioorganic & medicinal chemistry 20050201

Title: Distribution of BPA and metabolic assessment in glioblastoma patients during BNCT treatment: a microdialysis study.

Journal: Journal of neuro-oncology 20050201

Title: Biodistribution of boron compounds in an animal model of human undifferentiated thyroid cancer for boron neutron capture therapy.

Journal: Molecular pharmaceutics 20050101

Title: Boron neutron capture therapy for undifferentiated thyroid carcinoma: preliminary results with the combined use of BPA and BOPP.

Journal: Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20041101

Title: Biodistribution of p-borophenylalanine (BPA) in dogs with spontaneous undifferentiated thyroid carcinoma (UTC).

Journal: Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20041101

Title: The effect of dexamethasone on the uptake of p-boronophenylalanine in the rat brain and intracranial 9L gliosarcoma.

Journal: Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20041101

Title: Radiobiology of BNCT mediated by GB-10 and GB-10+BPA in experimental oral cancer.

Journal: Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20041101

Title: BNCT of 3 cases of spontaneous head and neck cancer in feline patients.

Journal: Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20041101

Title: Effects of boron neutron capture irradiation on the normal lung of rats.

Journal: Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20041101

Title: Boronated epidermal growth factor as a delivery agent for neutron capture therapy of EGF receptor positive gliomas.

Journal: Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20041101

Title: Tolerance of normal human brain to boron neutron capture therapy.

Journal: Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20041101

Title: Boron-containing nucleosides as potential delivery agents for neutron capture therapy of brain tumors.

Journal: Cancer research 20040901

Title: Delivery of (10)boron to oral squamous cell carcinoma using boronophenylalanine and borocaptate sodium for boron neutron capture therapy.

Journal: Oral oncology 20040501

Title: Biodistribution of GB-10 (Na(2)(10)B10H10 compound for boron neutron capture therapy (BNCT) in an experimental model of oral cancer in the hamster cheek pouch.

Journal: Archives of oral biology 20040401

Title: Analysis of boron-10 in soft tissue by dynamic secondary ion mass spectrometry.

Journal: Journal of microscopy 20040101

Title: Boron neutron capture therapy (BNCT) for malignant melanoma with special reference to absorbed doses to the normal skin and tumor.

Journal: Australasian physical & engineering sciences in medicine 20030901

Title: The enhancement of neutron irradiation of HeLa-S cervix carcinoma cells by cell-nucleus-addressed deca-p-boronophenylalanine.

Journal: European journal of medicinal chemistry 20030601

Title: 1H MRS of a boron neutron capture therapy 10B-carrier, L-p-boronophenylalanine-fructose complex, BPA-F: phantom studies at 1.5 and 3.0 T.

Journal: Physics in medicine and biology 20030421

Title: Effects of bisphenol A on antigen-specific antibody production, proliferative responses of lymphoid cells, and TH1 and TH2 immune responses in mice.

Journal: British journal of pharmacology 20030401

Title: Clinical implementation of 4-dihydroxyborylphenylalanine synthesised by an asymmetric pathway.

Journal: European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences 20030201

Title: Potential of alpha-amino alcohol p-boronophenylalaninol as a boron carrier in boron neutron capture therapy, regarding its enantiomers.

Journal: Journal of cancer research and clinical oncology 20030101

Title: Ligand liposomes and boron neutron capture therapy.

Journal: Journal of neuro-oncology 20030101

Title: Boron neutron capture therapy for glioblastoma multiforme: clinical studies in Sweden.

Journal: Journal of neuro-oncology 20030101

Title: Cell cycle dependence of boron uptake from two boron compounds used for clinical neutron capture therapy.

Journal: Cancer letters 20021210

Title: Long-term infusions of p-boronophenylalanine for boron neutron capture therapy: evaluation using rat brain tumor and spinal cord models.

Journal: Radiation research 20021201

Title: Impact of the p53 status of the tumor cells on the effect of reactor neutron beam irradiation, with emphasis on the response of intratumor quiescent cells.

Journal: Japanese journal of cancer research : Gann 20021201

Title: Direct synthesis of unprotected 4-aryl phenylalanines via the Suzuki reaction under microwave irradiation.

Journal: Organic letters 20021031

Title: Determination of boron-containing compounds in urine and blood plasma from boron neutron capture therapy patients. The importance of using coupled techniques.

Journal: Analytical chemistry 20021015

Title: Mutagenic effect of borocaptate sodium and boronophenylalanine in neutron capture therapy.

Journal: International journal of radiation oncology, biology, physics 20021001

Title: Improved treatment planning for boron neutron capture therapy for glioblastoma multiforme using fluorine-18 labeled boronophenylalanine and positron emission tomography.

Journal: Medical physics 20021001

Title: Imaging of fluorine and boron from fluorinated boronophenylalanine in the same cell at organelle resolution by correlative ion microscopy and confocal laser scanning microscopy.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20020801

Title: Quantitative subcellular secondary ion mass spectrometry (SIMS) imaging of boron-10 and boron-11 isotopes in the same cell delivered by two combined BNCT drugs: in vitro studies on human glioblastoma T98G cells.

Journal: Radiation research 20020601

Title: Non-linear model for the kinetics of 10B in blood after BPA-fructose complex infusion.

Journal: Physics in medicine and biology 20020307

Title: Neutron capture therapy of intracerebral melanoma: enhanced survival and cure after blood-brain barrier opening to improve delivery of boronophenylalanine.

Journal: International journal of radiation oncology, biology, physics 20020301

Title: Effect of boron neutron capture therapy for melanotic and amelanotic melanoma transplanted into mouse brain.

Journal: Pigment cell research 20020201

Title: Selective uptake of p-borophenylalanine by undifferentiated thyroid carcinoma for boron neutron capture therapy.

Journal: Thyroid : official journal of the American Thyroid Association 20020101

Title: Boron neutron capture therapy for the treatment of oral cancer in the hamster cheek pouch model.

Journal: Cancer research 20011215

Title: The hamster cheek pouch as a model of oral cancer for boron neutron capture therapy studies: selective delivery of boron by boronophenylalanine.

Journal: Cancer research 20011215

Title: Quantitative imaging and microlocalization of boron-10 in brain tumors and infiltrating tumor cells by SIMS ion microscopy: relevance to neutron capture therapy.

Journal: Cancer research 20011115

Title: Evaluation of apoptosis and micronucleation induced by reactor neutron beams with two different cadmium ratios in total and quiescent cell populations within solid tumors.

Journal: International journal of radiation oncology, biology, physics 20011101

Title: Atomic emission method for total boron in blood during neutron-capture therapy.

Journal: Clinical chemistry 20011001

Title: Evaluation of the genotoxic effects of the boron neutron capture reaction in human melanoma cells using the cytokinesis block micronucleus assay.

Journal: Mutagenesis 20010901

Title: Boronated dipeptide borotrimethylglycylphenylalanine as a potential boron carrier in boron neutron capture therapy for malignant brain tumors.

Journal: Radiation research 20010701

Title: Boron neutron capture therapy of a murine mammary carcinoma using a lipophilic carboranyltetraphenylporphyrin.

Journal: Radiation research 20010401

Title: A pharmacokinetic model for the concentration of 10B in blood after boronophenylalanine-fructose administration in humans.

Journal: Radiation research 20010401

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Tags:76410-58-7 Molecular Formula|76410-58-7 MDL|76410-58-7 SMILES|76410-58-7 4-Borono-L-phenylalanine