17755
4-Borono-L-phenylalanine
≥95.0% (HPLC)
Synonym(s):
4-Dihydroxyboryl-L-phenylalanine, L-BPA
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About This Item
Empirical Formula (Hill Notation):
C9H12BNO4
CAS Number:
Molecular Weight:
209.01
Beilstein:
4458616
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.21
Quality Level
Assay
≥95.0% (HPLC)
storage temp.
2-8°C
SMILES string
N[C@@H](Cc1ccc(cc1)B(O)O)C(O)=O
InChI
1S/C9H12BNO4/c11-8(9(12)13)5-6-1-3-7(4-2-6)10(14)15/h1-4,8,14-15H,5,11H2,(H,12,13)/t8-/m0/s1
InChI key
NFIVJOSXJDORSP-QMMMGPOBSA-N
Application
4-Borono-L-phenylalanine can be used as a building block in solid-phase peptide synthesis. It can also be used to synthesize substituted triazine derivatives as potential tryptophan hydroxylase inhibitors via Suzuki cross-coupling reaction using palladium as a catalyst.
Other Notes
Tyrosine analogue; employed for treatment of melanom cells by boron neutron capture therapy
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Genro Kashino et al.
Journal of radiation research, 50(4), 377-382 (2009-06-10)
Background and Purpose; (10)B deriving from (10)B-para-boronophenylalanine (BPA) and (10)B-borocaptate sodium (BSH) have been detected in blood samples of patients undergoing boron neutron capture therapy (BNCT) using prompt gamma ray spectrometer or Inductively Coupled Plasma (ICP) method, respectively. However, the
Y C Lin et al.
Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine, 69(12), 1728-1731 (2011-03-12)
This study attempted to increase the boron uptake of human head and neck carcinoma SAS cells for BNCT by using a gamma dose of 0.1 Gy for combined treatment. Intracellular boron concentrations in 25 μgB/mL medium of BPA treated and
Chang C Liu et al.
Journal of the American Chemical Society, 131(28), 9616-9617 (2009-06-27)
We recently developed a phage-based system for the evolution of proteins in bacteria with expanded amino acid genetic codes. Here we demonstrate that the unnatural amino acid p-boronophenylalanine (BF) confers a selective advantage in the evolution of glycan-binding proteins. We
Maria Alejandra Dagrosa et al.
International journal of radiation oncology, biology, physics, 79(1), 262-268 (2010-10-12)
DNA lesions produced by boron neutron capture therapy (BNCT) and those produced by gamma radiation in a colon carcinoma cell line were analyzed. We have also derived the relative biologic effectiveness factor (RBE) of the neutron beam of the RA-3-
Yuko Kinashi et al.
Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine, 163, 109204-109204 (2020-06-21)
Temozolomide (TMZ) is a DNA-alkylating agent used for chemo-radiotherapy of glioblastoma, which is also a target cancer for boron neutron capture therapy (BNCT). Although the DNA-repair enzyme O6-methylguanine DNA methyltransferase (MGMT) and the tumor suppressor p53 are mutated in some
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