Boc-O-benzyl-L-serine 4-nitrophenyl ester
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Boc-O-benzyl-L-serine 4-nitrophenyl ester

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Category
BOC-Amino Acids
Catalog number
BAT-002861
CAS number
16948-39-3
Molecular Formula
C21H24N2O7
Molecular Weight
416.43
Boc-O-benzyl-L-serine 4-nitrophenyl ester
IUPAC Name
(4-nitrophenyl) (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylmethoxypropanoate
Synonyms
Boc-L-Ser(Bzl)-Onp; 4-nitrophenyl (2S)-3-(benzyloxy)-2-{[(tert-butoxy)carbonyl]amino}propanoate
Appearance
Clear, yellow oil
Purity
≥ 99% (Elemental analysis)
Storage
Store at 2-8°C
InChI
InChI=1S/C21H24N2O7/c1-21(2,3)30-20(25)22-18(14-28-13-15-7-5-4-6-8-15)19(24)29-17-11-9-16(10-12-17)23(26)27/h4-12,18H,13-14H2,1-3H3,(H,22,25)/t18-/m0/s1
InChI Key
CLAREYWIWVFFND-SFHVURJKSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(COCC1=CC=CC=C1)C(=O)OC2=CC=C(C=C2)[N+](=O)[O-]
2. Radiosynthesis of O-(1-[18 F]fluoropropan-2-yl)-O-(4-nitrophenyl)methylphosphonate: A novel PET tracer surrogate of sarin
Thomas R Hayes, Charles M Thompson, Joseph E Blecha, John M Gerdes, Henry F VanBrocklin J Labelled Comp Radiopharm. 2018 Dec;61(14):1089-1094. doi: 10.1002/jlcr.3688. Epub 2018 Nov 4.
O-(1-Fluoropropan-2-yl)-O-(4-nitrophenyl) methylphosphonate is a reactive organophosphate ester (OP) developed as a surrogate of the chemical warfare agent sarin that forms a similar covalent adduct at the active site serine of acetylcholinesterase. The radiolabeled O-(1-[18 F]fluoropropan-2-yl)-O-(4-nitrophenyl) methylphosphonate ([18 F] fluorosarin surrogate) has not been previously prepared. In this paper, we report the first radiosynthesis of this tracer from the reaction of bis-(4-nitrophenyl) methylphosphonate with 1-[18 F]fluoro-2-propanol in the presence of DBU. The 1-[18 F]fluoro-2-propanol was prepared by reaction of propylene sulfite with Kryptofix 2.2.2 and [18 F] fluoride ion. The desired tracer O-(1-[18 F]fluoropropan-2-yl)-O-(4-nitrophenyl) methylphosphonate was obtained in a >98% radiochemical purity with a 2.4% ± 0.6% yield (n = 5, 65 minutes from start of synthesis) based on starting [18 F] fluoride ion and a molar activity of 49.9 GBq/μmol (1.349 ± 0.329 Ci/μmol, n = 3). This new facile radiosynthesis routinely affords sufficient quantities of [18 F] fluorosarin surrogate in high radiochemical purity, which will further enable the tracer development as a novel radiolabeled OP acetylcholinesterase inhibitor for assessment of OP modes of action with PET imaging in vivo.
3. β-Glucuronidase-coupled assays of glucuronoyl esterases
Lucia Fraňová, Vladimír Puchart, Peter Biely Anal Biochem. 2016 Oct 1;510:114-119. doi: 10.1016/j.ab.2016.07.023. Epub 2016 Jul 22.
Glucuronoyl esterases (GEs) are microbial enzymes with potential to cleave the ester bonds between lignin alcohols and xylan-bound 4-O-methyl-d-glucuronic acid in plant cell walls. This activity renders GEs attractive research targets for biotechnological applications. One of the factors impeding the progress in GE research is the lack of suitable substrates. In this work, we report a facile preparation of methyl esters of chromogenic 4-nitrophenyl and 5-bromo-4-chloro-3-indolyl β-D-glucuronides for qualitative and quantitative GE assay coupled with β-glucuronidase as the auxiliary enzyme. The indolyl derivative affording a blue indigo-type product is suitable for rapid and sensitive assay of GE in commercial preparations as well as for high throughput screening of microorganisms and genomic and metagenomic libraries.
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