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Sigma-Aldrich

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

Pictograms

Exclamation mark

Signal Word

Warning

Hazard 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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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
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-
Andrea Monti Hughes et al.
Oral oncology, 47(11), 1017-1022 (2011-08-16)
Given the clinical relevance of locoregional recurrences in head and neck cancer, we developed a novel experimental model of premalignant tissue in the hamster cheek pouch for long-term studies and demonstrated the partial inhibitory effect of a single application of
Rolf F Barth
Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine, 67(7-8 Suppl), S3-S6 (2009-05-27)
Over the past 25 years research on boron neutron capture therapy (BNCT) has progressed relatively slowly but steadily with the greatest progress in the field of clinical studies. These specifically have included the use of BNCT to treat a variety
Andrea Wittig et al.
Radiation research, 172(4), 493-499 (2009-09-24)
In boron neutron capture therapy, the absorbed dose from the (10)B(n,alpha)(7)Li reaction depends on the (10)B concentration and (10)B distribution in the irradiated volume. Thus compounds used in BNCT should have tumor-specific uptake and low accumulation in normal tissues. This

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