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H6759

Sigma-Aldrich

L-Histidine β-naphthylamide

≥98% (TLC)

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About This Item

Empirical Formula (Hill Notation):
C16H16N4O
CAS Number:
7424-15-9
Molecular Weight:
280.32
EC Number:
231-052-4
MDL number:
MFCD00051166
UNSPSC Code:
12352209
PubChem Substance ID:
24895761
NACRES:
NA.26

product name

L-Histidine β-naphthylamide, powder

assay

≥98% (TLC)

form

powder

color

white to faint yellow

storage temp.

−20°C

SMILES string

N[C@@H](Cc1cnc[nH]1)C(=O)Nc2ccc3ccccc3c2

InChI

1S/C16H16N4O/c17-15(8-14-9-18-10-19-14)16(21)20-13-6-5-11-3-1-2-4-12(11)7-13/h1-7,9-10,15H,8,17H2,(H,18,19)(H,20,21)/t15-/m0/s1

InChI key

DKDILZBBFKZMRO-HNNXBMFYSA-N

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Biochem/physiol Actions

L-Histidine β-naphthylamide is an analogue of L-histidine used to study structural roles of L-histidine in functions such as the activation of HutP protein transcription. L-Histidine β-naphthylamide may also be used to study the specificity and kinetics of various proteases and peptidases.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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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Allosteric activation of HutP protein, that regulates transcription of hut operon in Bacillus subtilis, mediated by various analogs of histidine.
Kumarevel T, Mizuno H, Kumar PK.
Nucleic Acids Research, 3, 199-200 (2003)
X Iturrioz et al.
Biochemistry, 39(11), 3061-3068 (2000-03-15)
Aminopeptidase A (EC 3.4.11.7, APA) is a 130 kDa membrane-bound protease that contains the HEXXH consensus sequence found in the zinc metalloprotease family, the zincins. In addition to the catalytic zinc atom, APA contains a Ca2+ ion that increases its
R A Field et al.
The Biochemical journal, 274 ( Pt 3), 885-889 (1991-03-15)
This present study reports the ability of a range of derivatives of L-histidine, histamine and imidazole to act as inhibitors of sweet-almond beta-glucosidase, yeast alpha-glucosidase and Escherichia coli beta-galactosidase. The addition of a hydrophobic group to the basic imidazole nucleus
Endang Setyorini et al.
Journal of basic microbiology, 46(4), 294-304 (2006-07-19)
A halotolerant strain FP-133, able to grow at concentrations of 0-12.5% (w/v) NaCl, was isolated from a fish paste and identified as Bacillus subtilis . B. subtilis strain FP-133 produced an intracellular protease which showed catalytic activity under saline conditions.

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