Nα-Boc-L-asparagine 4-nitrophenyl ester
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Nα-Boc-L-asparagine 4-nitrophenyl ester

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Category
BOC-Amino Acids
Catalog number
BAT-002925
CAS number
4587-33-1
Molecular Formula
C15H19N3O7
Molecular Weight
353.30
Nα-Boc-L-asparagine 4-nitrophenyl ester
IUPAC Name
(4-nitrophenyl) (2S)-4-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoate
Synonyms
Boc-L-Asn-ONp; BOC-ASPARAGINE-ONP; Boc-Asn-p-nitrophenyl ester; BOC-L-ASPARTIC ACID-OH; N-T-BUTOXYCARBONYL-L-ASPATIC ACID; p-nitrophenyl (S)-2-tert-butoxycarbonylamino-3-carbamoylpropanoate
Appearance
White to off-white powder
Purity
≥ 98% (HPLC)
Density
1.318±0.06 g/cm3
Melting Point
140-155 °C
Boiling Point
609.3±55.0 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C15H19N3O7/c1-15(2,3)25-14(21)17-11(8-12(16)19)13(20)24-10-6-4-9(5-7-10)18(22)23/h4-7,11H,8H2,1-3H3,(H2,16,19)(H,17,21)/t11-/m0/s1
InChI Key
IAPXDJMULQXGDD-NSHDSACASA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CC(=O)N)C(=O)OC1=CC=C(C=C1)[N+](=O)[O-]

Nα-Boc-L-asparagine 4-nitrophenyl ester is a specialized reagent used in organic synthesis and peptide chemistry. Here are some key applications of Nα-Boc-L-asparagine 4-nitrophenyl ester:

Peptide Synthesis: This reagent is commonly used in the solid-phase synthesis of peptides. It serves as a protected amino acid building block, enabling the incorporation of asparagine residues in growing peptide chains. The Boc protecting group ensures selective reactions, while the 4-nitrophenyl ester acts as a leaving group, facilitating peptide bond formation.

Enzyme Activity Studies: Nα-Boc-L-asparagine 4-nitrophenyl ester can be used as a substrate to measure enzyme activity, particularly for enzymes that catalyze deprotection or hydrolysis reactions. The release of the 4-nitrophenyl group upon enzymatic action can be monitored spectrophotometrically, providing quantitative data on enzyme kinetics. This application is valuable in enzymology research and drug discovery.

Development of Synthetic Analogs: Researchers use Nα-Boc-L-asparagine 4-nitrophenyl ester as an intermediate in the synthesis of various analogs and derivatives of asparagine-containing compounds. These synthetic analogs can be tested for potential biological activity or as starting materials for further chemical modifications. This aids in the development of new therapeutic agents and biochemical probes.

Protein Engineering: In protein engineering, this compound can be utilized to introduce asparagine analogs into proteins. By replacing natural asparagine with modified residues, scientists can study the impact on protein stability, folding, and function. This application is essential in understanding protein structure-function relationships and designing proteins with improved properties.

2. 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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