All Photos(1)
Synonym(s):
4-Dihydroxyboryl-L-phenylalanine, L-BPA
Empirical Formula (Hill Notation):
C9H12BNO4
CAS Number:
Molecular Weight:
209.01
Beilstein:
4458616
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.21
Recommended Products
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
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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Ana J Molinari et al.
Radiation research, 177(1), 59-68 (2011-10-11)
We previously demonstrated the efficacy of BNCT mediated by boronophenylalanine (BPA) to treat tumors in a hamster cheek pouch model of oral cancer with no normal tissue radiotoxicity and moderate, albeit reversible, mucositis in precancerous tissue around treated tumors. It
T Fujimoto et al.
Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine, 69(12), 1713-1716 (2011-03-01)
Clear cell sarcoma (CCS), a rare malignant tumor with a predilection for young adults, is of poor prognosis. Recently however, boron neutron capture therapy (BNCT) with the use of p-borono-L-phenylalanine (BPA) for malignant melanoma has provided good results. CCS also
C. Malan et al.
The Journal of Organic Chemistry, 63, 8019-8019 (1998)
Tsubasa Watanabe et al.
BMC cancer, 16(1), 859-859 (2016-11-09)
Boron neutron capture therapy (BNCT) is a cellular-level particle radiation therapy that combines the selective delivery of boron compounds to tumour tissue with neutron irradiation. L-p-Boronophenylalanine (L-BPA) is a boron compound now widely used in clinical situations. Determination of the
Substituted 3-(4-(1, 3, 5-triazin-2-yl)-phenyl)-2-aminopropanoic acids as novel tryptophan hydroxylase inhibitors
Jin Haihong, et al.
Bioorganic & Medicinal Chemistry Letters, 19(17), 5229-5232 (2009)
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