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14408

Sigma-Aldrich

N-(+)-Biotinyl-4-aminobenzoic acid

≥98.0% (HPLC)

Synonym(s):

B-PABA

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About This Item

Empirical Formula (Hill Notation):
C17H21N3O4S
CAS Number:
6929-40-4
Molecular Weight:
363.43
Beilstein:
50100
MDL number:
MFCD00077915
UNSPSC Code:
12352106
eCl@ss:
34058011
PubChem Substance ID:
57647153
NACRES:
NA.79

Quality Level

200

Assay

≥98.0% (HPLC)

form

powder

optical activity

[α]20/D +55±3°, c = 0.5% in 0.1 M NaOH

color

white to light yellow

mp

295-297 °C

storage temp.

2-8°C

SMILES string

[H][C@]12CS[C@@H](CCCCC(=O)Nc3ccc(cc3)C(O)=O)[C@@]1([H])NC(=O)N2

InChI

1S/C17H21N3O4S/c21-14(18-11-7-5-10(6-8-11)16(22)23)4-2-1-3-13-15-12(9-25-13)19-17(24)20-15/h5-8,12-13,15H,1-4,9H2,(H,18,21)(H,22,23)(H2,19,20,24)/t12-,13-,15-/m0/s1

InChI key

PVMDAMXGKHIMSQ-YDHLFZDLSA-N

Biochem/physiol Actions

Biotinyl-4-aminobenzoic acid (B-PABA) is used as a substrate in biotinidase assays.

Other Notes

Enzyme substrate used in the assay of biotinidase

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Determination of biotinidase activity by liquid chromatography with fluorimetric detection.
K Hayakawa et al.
Journal of chromatography, 383(1), 148-152 (1986-11-28)
Keyna A Kobza et al.
The Journal of nutritional biochemistry, 19(12), 826-832 (2008-05-16)
Posttranslational modification of histones by biotinylation can be catalyzed by both biotinidase (BTD) and holocarboxylase synthetase. Biotinylation of histones is an important epigenetic mechanism to regulate gene expression, DNA repair, and chromatin remodeling. The role of BTD in histone biotinylation
D V Craft et al.
Biochemistry, 24(10), 2471-2476 (1985-05-07)
Biotinidase catalyzes the hydrolysis of N epsilon-biotinyllysine (biocytin) to form biotin and free lysine. The enzyme has been purified 4800-fold from outdated human plasma and was determined by sodium dodecyl sulfate-polyacrylamide gel electrophoresis to have a molecular weight of (76
D T Forman et al.
Annals of clinical and laboratory science, 22(3), 144-154 (1992-05-11)
Children with juvenile-onset multiple carboxylase deficiency lack biotinidase activity (biotinamide amidohydrolase, EC 3.5.1.12) in the liver and other tissues. Hence, little free biotin is metabolically available, resulting in seizures, acidosis, and serious neurological damage. As the absence of hepatic biotinidase

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