Boc-D-alanine-4-nitrophenyl ester
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Boc-D-alanine-4-nitrophenyl ester

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Category
BOC-Amino Acids
Catalog number
BAT-000394
CAS number
85546-27-6
Molecular Formula
C14H18N2O6
Molecular Weight
310.31
IUPAC Name
(4-nitrophenyl) (2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
Synonyms
Boc-D-Ala-Onp; (R)-4-Nitrophenyl 2-((tert-butoxycarbonyl)amino)propanoate
Purity
≥ 99% (HPLC)
Melting Point
144-152 °C
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-/m1/s1
InChI Key
SUHFNHHZORGDFI-SECBINFHSA-N
Canonical SMILES
CC(C(=O)OC1=CC=C(C=C1)[N+](=O)[O-])NC(=O)OC(C)(C)C

Boc-D-alanine-4-nitrophenyl ester, a derivative of D-alanine with protective properties, finds diverse applications in biochemistry. Here are the key applications presented with a high degree of perplexity and burstiness:

Peptide Synthesis: A cornerstone of peptide synthesis, Boc-D-alanine-4-nitrophenyl ester serves as a vital amino acid building block. It introduces a shielded D-alanine residue into peptides circumventing undesired side reactions. This compound enables precise management during peptide elongation, ensuring impeccable fidelity and yield in the production of synthetic peptides.

Enzyme Assays: Embedded in biochemical exploration, Boc-D-alanine-4-nitrophenyl ester emerges as a pivotal substrate for enzyme assays particularly pertinent to proteases. The enzymatic cleavage of the ester bond releases a detectable nitrophenol byproduct, aiding in the quantification of enzyme activity. This illuminates enzyme kinetics and specificity providing deeper insights for researchers.

Drug Development: Spearheading drug development initiatives, Boc-D-alanine-4-nitrophenyl ester plays a key role in analyzing enzyme-inhibitor interactions. By leveraging this compound as a substrate, researchers can evaluate the inhibitory effects of potential drug candidates on specific enzymes. This data is indispensable for crafting efficacious enzyme inhibitors tailored for therapeutic use.

Chemical Biology: Exerting a significant influence in the realm of chemical biology, Boc-D-alanine-4-nitrophenyl ester proves invaluable for probing protein modifications and interactions. It enables the targeted modification of proteins at specific sites, facilitating the scrutiny of protein functionalities and interaction networks. This application is pivotal for unraveling intricate biological processes and devising precision interventions.

1. 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.
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. 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.
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