776181
3-(2-Acetoxy-4,6-dimethylphenyl)-3-methylbutyric acid N-succinimidyl ester
95%
Synonym(s):
3-(2-Acetoxy-4,6-dimethylphenyl)-3-methylbutyric acid N-hydroxysuccinimide ester, Trimethyl lock NHS, Trimethyl lock succinimidyl ester
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About This Item
Empirical Formula (Hill Notation):
C19H23NO6
Molecular Weight:
361.39
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352106
MDL number:
Assay:
95%
Form:
solid
InChI
1S/C19H23NO6/c1-11-8-12(2)18(14(9-11)25-13(3)21)19(4,5)10-17(24)26-20-15(22)6-7-16(20)23/h8-9H,6-7,10H2,1-5H3
SMILES string
CC(=O)Oc1cc(C)cc(C)c1C(C)(C)CC(=O)ON2C(=O)CCC2=O
InChI key
KMNOKEFBKJGRFL-UHFFFAOYSA-N
assay
95%
form
solid
mp
107-112 °C
storage temp.
2-8°C
Quality Level
Application
This ′trimethyl lock′ derivative is activated with a succinimidyl ester for modification of amine containing compounds and biomolecules. After modification of your amine of interest, your now ′masked′ molecule can be released by cleavage of the ester, which can be achieved by cellular esterases. This triggers a rapid lactonization reaction of the ′trimethyl lock′ to regenerate your original amine-containing molecule. This approach has been applied to release of fluorophores, peptides, nucleic acids as well as small molecule drugs.
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Michael N Levine et al.
Chemical science, 3(8), 2412-2420 (2012-11-28)
The trimethyl lock is an o-hydroxydihydrocinnamic acid derivative in which unfavorable steric interactions between three pendant methyl groups encourage lactonization to form a hydrocoumarin. This reaction is extremely rapid, even when the electrophile is an amide and the leaving group
Michael N Levine et al.
Molecules (Basel, Switzerland), 13(2), 204-211 (2008-02-29)
p-Nitrophenyl acetate is the most commonly used substrate for detecting the catalytic activity of esterases, including those that activate prodrugs in human cells. This substrate is unstable in aqueous solution, limiting its utility. Here, a stable chromogenic substrate for esterases
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