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53298

Sigma-Aldrich

Methyl 4-methylumbelliferyl hexylphosphonate

≥95.0% (HPLC)

Synonym(s):

Hexylphosphonic acid methyl 4-methylumbelliferyl ester

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About This Item

Empirical Formula (Hill Notation):
C17H23O5P
CAS Number:
1575736-03-6
Molecular Weight:
338.34
UNSPSC Code:
12352204
PubChem Substance ID:
329757930
NACRES:
NA.77

Assay

≥95.0% (HPLC)

storage temp.

−20°C

SMILES string

O=P(OC)(CCCCCC)OC1=CC=C(C(C)=CC(O2)=O)C2=C1

InChI

1S/C17H23O5P/c1-4-5-6-7-10-23(19,20-3)22-14-8-9-15-13(2)11-17(18)21-16(15)12-14/h8-9,11-12H,4-7,10H2,1-3H3

InChI key

UDTZADITECBVLJ-UHFFFAOYSA-N

Application

This lipase suicide inhibitor can be utilized to determine lipase and hydrolase activity, even in complex protein mixtures. The molar amount of enzyme can be determined by active site titration experiments. This inhibitor is soluble in both DMF and DMSO. Active site titrations should be performed in a pH range from 7-8 considering that higher pH values can lead to appreciable spontaneous hydrolysis. It is recommended to perform corresponding negative controls (buffer only).

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCBV5960
BCBP6377
BCBP6377V
BCBR1680V

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Zi Jin et al.
Analytical biochemistry, 450, 46-48 (2014-01-11)
We describe a method for quantification of displayed lipase on yeast cell surface. The strategy uses an organophosphonate ester to irreversibly inhibit the active lipase and release a detectable fluorescent group. The amount of displayed lipase can be represented as
Lipase chemoselectivity towards alcohol and thiol acyl acceptors in a transacylation reaction
Hedfors, C., et al.
Journal of Molecular Catalysis. B, Enzymatic, 66, 120-123 (2010)
Active-site titration analysis of surface influences on immobilized Candida antarctica lipase B activity
Laszlo, J. A., et al.
Journal of Molecular Catalysis. B, Enzymatic, 69, 60-65 (2011)
Zhen Qian et al.
Chembiochem : a European journal of chemical biology, 8(16), 1989-1996 (2007-09-19)
The engineering of lipase B from Candida antarctica (CALB) by circular permutation has yielded over sixty hydrolase variants, and several show significantly improved catalytic performance. Here we report a detailed characterization of ten selected enzyme variants by kinetic and spectroscopic
Anders O Magnusson et al.
Chembiochem : a European journal of chemical biology, 6(6), 1051-1056 (2005-05-11)
The active site of Candida antarctica lipase B (CALB) hosts the catalytic triad (Ser-His-Asp), an oxyanion hole and a stereospecificity pocket. During catalysis, the fast-reacting enantiomer of secondary alcohols places its medium-sized substituent in the stereospecificity pocket and its large

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