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Merck
CN

27525

L-Citrulline 7-amido-4-methylcoumarin hydrobromide

≥98.0% (sum of enantiomers, HPLC)

Synonym(s):

L-Citrulline 4-methyl-7-coumarinylamide hydrobromide

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About This Item

Empirical Formula (Hill Notation):
C16H20N4O4 · HBr
CAS Number:
123314-39-6
Molecular Weight:
413.27
UNSPSC Code:
12352209
PubChem Substance ID:
329753001
MDL number:
MFCD00152040

Key Documents

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InChI

1S/C16H20N4O4.BrH/c1-9-7-14(21)24-13-8-10(4-5-11(9)13)20-15(22)12(17)3-2-6-19-16(18)23;/h4-5,7-8,12H,2-3,6,17H2,1H3,(H,20,22)(H3,18,19,23);1H/t12-;/m0./s1

SMILES string

Br[H].CC1=CC(=O)Oc2cc(NC(=O)[C@@H](N)CCCNC(N)=O)ccc12

InChI key

XYOHUMXDURSJOW-YDALLXLXSA-N

assay

≥98.0% (sum of enantiomers, HPLC)

storage temp.

2-8°C

Quality Level

100

Application

L-Citrulline 7-amido-4-methylcoumarin is used as a sensitive fluorogenic substrate for citrulline ureidase, yielding a blue solution upon cleavage.

Other Notes

Substrate for proteases

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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J E Sheppeck et al.
Bioorganic & medicinal chemistry letters, 10(23), 2639-2642 (2000-12-29)
A statistically exhaustive, 8800 compound tripeptidal amidomethylcoumarin library was synthesized as discreet compounds using solid-phase combinatorial chemistry. A subset of the compounds was purified by HPLC and tested in a high-throughput fluorometric assay against several known serine and cysteine proteases
N J MARCHETTE et al.
Journal of bacteriology, 82, 26-32 (1961-07-01)
Marchette, Nyven J. (University of Utah, Salt Lake City), and Paul S. Nicholes. Virulence and citrulline ureidase activity of Pasteurella tularensis. J. Bacteriol. 82:26-32. 1961.-The presence of a citrulline ureidase system in Pasteurella tularensis strains of high virulence, and its
J E Clarridge et al.
Journal of clinical microbiology, 34(8), 1995-2000 (1996-08-01)
We have isolated two phenotypically distinct nonfastidious Francisella strains (Fx1 and Fx2) from the blood of compromised patients with pneumonia and compared them with eight other Francisella strains, including Francisella tularensis biovar tularensis, F. tularensis biovar novicida, and F. philomiragia.
Manish Mahawar et al.
Journal of bacteriology, 191(15), 4798-4806 (2009-06-09)
The citrulline ureidase (CTU) activity has been shown to be associated with highly virulent Francisella tularensis strains, including Schu S4, while it is absent in avirulent or less virulent strains. A definitive role of the ctu gene in virulence and

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