Boc-L-alanine-4-nitrophenyl ester
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Boc-L-alanine-4-nitrophenyl ester

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Category
BOC-Amino Acids
Catalog number
BAT-002751
CAS number
2483-49-0
Molecular Formula
C14H18N2O6
Molecular Weight
310.31
Boc-L-alanine-4-nitrophenyl ester
IUPAC Name
(4-nitrophenyl) (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
Synonyms
Boc-L-Ala-Onp; N-Boc-L-alanine p-nitrophenyl ester
Appearance
Off-white or beige powder
Purity
≥ 98% (HPLC)
Density
1.237±0.06 g/cm3(Predicted)
Melting Point
71-73 °C
Boiling Point
460.9±30.0 °C(Predicted)
Storage
Store at 2-8 °C
InChI
InChI=1S/C14H18N2O6/c1-9(15-13(18)22-14(2,3)4)12(17)21-11-7-5-10(6-8-11)16(19)20/h5-9H,1-4H3,(H,15,18)/t9-/m0/s1
InChI Key
SUHFNHHZORGDFI-VIFPVBQESA-N
Canonical SMILES
CC(C(=O)OC1=CC=C(C=C1)[N+](=O)[O-])NC(=O)OC(C)(C)C

Boc-L-alanine-4-nitrophenyl ester is a versatile chemical compound, widely utilized in peptide synthesis and biochemical research. Explore its diverse applications with heightened perplexity and burstiness:

Peptide Synthesis: Acting as a crucial component in peptide synthesis, Boc-L-alanine-4-nitrophenyl ester serves as the foundation for initiating peptide chain assembly. Its reactive ester group streamlines the formation of peptide bonds, particularly when incorporating alanine residues into emerging peptide structures. This reagent plays a pivotal role in meticulously crafting peptides with exceptional specificity and purity.

Enzyme Assays: Delving into the realm of enzyme activity evaluation, Boc-L-alanine-4-nitrophenyl ester emerges as a pivotal substrate for monitoring proteolytic enzyme function. Upon enzymatic cleavage, the ester liberates a nitrophenol group allowing for precise quantitative analysis via spectrophotometry. This application is indispensable for probing enzyme kinetics dynamics and assessing inhibitor effectiveness with utmost precision.

Protein Engineering: Fostering advancements in protein manipulation, this compound facilitates the targeted incorporation of alanine residues into protein structures. Through strategic reactions between Boc-L-alanine-4-nitrophenyl ester and specific proteins, researchers can introduce alterations to protein sequences enabling in-depth investigations into structure-function correlations. These modifications play a critical role in unraveling and refining protein behavior for enhanced understanding and application.

Chemical Biology: Embracing the interdisciplinary realm of chemical biology, Boc-L-alanine-4-nitrophenyl ester emerges as a valuable asset for biomolecular labeling and tracking endeavors. The nitrophenyl group functions as a distinctive tag enabling the visualization and quantification of intricate biochemical interactions. This innovative tool empowers researchers to elucidate complex biological processes and unveil intricate biomolecular associations, paving the way for groundbreaking discoveries in the field.

1. Palladium-Catalyzed Tandem Ester Dance/Decarbonylative Coupling Reactions
Masayuki Kubo, Naomi Inayama, Eisuke Ota, Junichiro Yamaguchi Org Lett. 2022 Jun 3;24(21):3855-3860. doi: 10.1021/acs.orglett.2c01432. Epub 2022 May 23.
"Dance reaction" on the aromatic ring is a powerful method in organic chemistry to translocate functional groups on arene scaffolds. Notably, dance reactions of halides and pseudohalides offer a unique platform for the divergent synthesis of substituted (hetero)aromatic compounds when combined with transition-metal-catalyzed coupling reactions. Herein, we report a tandem reaction of ester dance and decarbonylative coupling enabled by palladium catalysis. In this reaction, 1,2-translocation of the ester moiety on the aromatic ring is followed by decarbonylative coupling with nucleophiles to enable the installation of a variety of nucleophiles at the position adjacent to the ester in the starting material.
2. Lactose esters: synthesis and biotechnological applications
Jakub Staroń, Janusz M Dąbrowski, Ewelina Cichoń, Maciej Guzik Crit Rev Biotechnol. 2018 Mar;38(2):245-258. doi: 10.1080/07388551.2017.1332571. Epub 2017 Jun 6.
Biodegradable nonionic sugar esters-based surfactants have been gaining more and more attention in recent years due to their chemical plasticity that enables the various applications of these molecules. In this review, various synthesis methods and biotechnological implications of lactose esters (LEs) uses are considered. Several chemical and enzymatic approaches are described for the synthesis of LEs, together with their applications, i.e. function in detergents formulation and as additives that not only stabilize food products but also protect food from undesired microbial contamination. Further, this article discusses medical applications of LEs in cancer treatment, especially their uses as biosensors, halogenated anticancer drugs, and photosensitizing agents for photodynamic therapy of cancer and photodynamic inactivation of microorganisms.
3. A Ketone Ester Drink Lowers Human Ghrelin and Appetite
Brianna J Stubbs, Pete J Cox, Rhys D Evans, Malgorzata Cyranka, Kieran Clarke, Heidi de Wet Obesity (Silver Spring). 2018 Feb;26(2):269-273. doi: 10.1002/oby.22051. Epub 2017 Nov 6.
Objective: The ketones d-β-hydroxybutyrate (BHB) and acetoacetate are elevated during prolonged fasting or during a "ketogenic" diet. Although weight loss on a ketogenic diet may be associated with decreased appetite and altered gut hormone levels, it is unknown whether such changes are caused by elevated blood ketones. This study investigated the effects of an exogenous ketone ester (KE) on appetite. Methods: Following an overnight fast, subjects with normal weight (n = 15) consumed 1.9 kcal/kg of KE, or isocaloric dextrose (DEXT), in drinks matched for volume, taste, tonicity, and color. Blood samples were analyzed for BHB, glucose, insulin, ghrelin, glucagon-like peptide 1 (GLP-1), and peptide tyrosine tyrosine (PYY), and a three-measure visual analogue scale was used to measure hunger, fullness, and desire to eat. Results: KE consumption increased blood BHB levels from 0.2 to 3.3 mM after 60 minutes. DEXT consumption increased plasma glucose levels between 30 and 60 minutes. Postprandial plasma insulin, ghrelin, GLP-1, and PYY levels were significantly lower 2 to 4 hours after KE consumption, compared with DEXT consumption. Temporally related to the observed suppression of ghrelin, reported hunger and desire to eat were also significantly suppressed 1.5 hours after consumption of KE, compared with consumption of DEXT. Conclusions: Increased blood ketone levels may directly suppress appetite, as KE drinks lowered plasma ghrelin levels, perceived hunger, and desire to eat.
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