Z-3-aminobenzoic acid N-hydroxysuccinimide ester
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Z-3-aminobenzoic acid N-hydroxysuccinimide ester

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Category
CBZ-Amino Acids
Catalog number
BAT-005747
CAS number
129666-48-4
Molecular Formula
C19H16N2O6
Molecular Weight
368.68
Z-3-aminobenzoic acid N-hydroxysuccinimide ester
IUPAC Name
(2,5-dioxopyrrolidin-1-yl) 3-(phenylmethoxycarbonylamino)benzoate
Synonyms
Z-3-Abz-OSu
Appearance
Off-white powder
Purity
≥ 98% (TLC)
Melting Point
142-149 °C
Storage
Store at 2-8°C
InChI
InChI=1S/C19H16N2O6/c22-16-9-10-17(23)21(16)27-18(24)14-7-4-8-15(11-14)20-19(25)26-12-13-5-2-1-3-6-13/h1-8,11H,9-10,12H2,(H,20,25)
InChI Key
GTEFLNWIEFSKDY-UHFFFAOYSA-N
Canonical SMILES
C1CC(=O)N(C1=O)OC(=O)C2=CC(=CC=C2)NC(=O)OCC3=CC=CC=C3
1. Selective protein N-terminal labeling with N-hydroxysuccinimide esters
Hanjie Jiang, Gabriel D D'Agostino, Philip A Cole, Daniel R Dempsey Methods Enzymol. 2020;639:333-353. doi: 10.1016/bs.mie.2020.04.018. Epub 2020 Apr 28.
In order to gain detailed insight into the biochemical behavior of proteins, researchers have developed chemical tools to incorporate new functionality into proteins beyond the canonical 20 amino acids. Important considerations regarding effective chemical modification of proteins include chemoselectivity, near stoichiometric labeling, and reaction conditions that maintain protein stability. Taking these factors into account, we discuss an N-terminal labeling strategy that employs a simple two-step "one-pot" method using N-hydroxysuccinimide (NHS) esters. The first step converts a R-NHS ester into a more chemoselective R-thioester. The second step reacts the in situ generated R-thioester with a protein that harbors an N-terminal cysteine to generate a new amide bond. This labeling reaction is selective for the N-terminus with high stoichiometry. Herein, we provide a detailed description of this method and further highlight its utility with a large protein (>100kDa) and labeling with a commonly used cyanine dye.
2. A rapid and robust method for amino acid quantification using a simple N-hydroxysuccinimide ester derivatization and liquid chromatography-ion mobility-mass spectrometry
Taylor M Domenick, Austin L Jones, Robin H J Kemperman, Richard A Yost Anal Bioanal Chem. 2022 Jul;414(18):5549-5559. doi: 10.1007/s00216-022-03993-w. Epub 2022 Mar 26.
The vast majority of mass spectrometry (MS)-based metabolomics studies employ reversed-phase liquid chromatography (RPLC) to separate analytes prior to MS detection. Highly polar metabolites, such as amino acids (AAs), are poorly retained by RPLC, making quantitation of these key species challenging across the broad concentration ranges typically observed in biological specimens, such as cell extracts. To improve the detection and quantitation of AAs in microglial cell extracts, the implementation of a 4-dimethylaminobenzoylamido acetic acid N-hydroxysuccinimide ester (DBAA-NHS) derivatization agent was explored for its ability to improve both analyte retention and detection limits in RPLC-MS. In addition to the introduction of the DBAA-NHS labeling reagent, a uniformly (U) 13C-labeled yeast extract was also introduced during the sample preparation workflow as an internal standard (IS) to eliminate artifacts and to enable targeted quantitation of AAs, as well as untargeted amine submetabolome profiling. To improve method sensitivity and selectivity, multiplexed drift-tube ion mobility (IM) was integrated into the LC-MS workflow, facilitating the separation of isomeric metabolites, and improving the structural identification of unknown metabolites. Implementation of the U-13C-labeled yeast extract during the multiplexed LC-IM-MS analysis enabled the quantitation of 19 of the 20 common AAs, supporting a linear dynamic range spanning up to three orders of magnitude in concentration for microglial cell extracts, in addition to reducing the required cell count for reliable quantitation from 10 to 5 million cells per sample.
3. Synthesis of Chiral TFA-Protected α-Amino Aryl-Ketone Derivatives with Friedel-Crafts Acylation of α-Amino Acid N-Hydroxysuccinimide Ester
Zetryana Puteri Tachrim, et al. Molecules. 2017 Oct 17;22(10):1748. doi: 10.3390/molecules22101748.
Chiral N-protected α-amino aryl-ketones are one of the useful precursors used in the synthesis of various biologically active compounds and can be constructed via Friedel-Crafts acylation of N-protected α-amino acids. One of the drawbacks of this reaction is the utilization of toxic, corrosive and moisture-sensitive acylating reagents. In peptide construction via amide bond formation, N-hydroxysuccinimide ester (OSu), which has high storage stability, can react rapidly with amino components and produces fewer side reactions, including racemization. This study reports the first synthesis and utilization of N-trifluoroacetyl (TFA)-protected α-amino acid-OSu as a potential acyl donor for Friedel-Crafts acylation into various arenes. The TFA-protected isoleucine derivative and its diastereomer TFA-protected allo-isoleucine derivative were investigated to check the retention of α-proton chirality in the Friedel-Crafts reaction. Further utilization of OSu in other branched-chain and unbranched-chain amino acids results in an adequate yield of TFA-protected α-amino aryl-ketone without loss of optical purity.
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