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Z-L-alanine-N-hydroxysuccinimide ester

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Category

CBZ-Amino Acids

Catalog number

BAT-003322

CAS number

3401-36-3

Molecular Formula

C15H16N2O6

Molecular Weight

320.30

IUPAC Name

(2,5-dioxopyrrolidin-1-yl) (2S)-2-(phenylmethoxycarbonylamino)propanoate

Synonyms

Z-L-Ala-Osu; N-[(Phenylmethoxy)Carbonyl]-,2,5-Dioxo-1-Pyrrolidinyl Ester

Appearance

White to off-white powder

Purity

≥ 99% (HPLC)

Density

1.36 g/cm3

Melting Point

120-124 °C

Storage

Store at-20 °C

InChI

InChI=1S/C15H16N2O6/c1-10(14(20)23-17-12(18)7-8-13(17)19)16-15(21)22-9-11-5-3-2-4-6-11/h2-6,10H,7-9H2,1H3,(H,16,21)/t10-/m0/s1

InChI Key

OFIYNISEFIEQBC-JTQLQIEISA-N

Canonical SMILES

CC(C(=O)ON1C(=O)CCC1=O)NC(=O)OCC2=CC=CC=C2

Z-L-alanine-N-hydroxysuccinimide ester, a commonly utilized reagent in biochemical and pharmaceutical research, serves various essential functions. Here are the key applications creatively explained with high perplexity and burstiness:

Peptide Synthesis: A cornerstone of biochemical endeavors, Z-L-alanine-N-hydroxysuccinimide ester plays a pivotal role in peptide creation orchestrating the intricate dance of peptide bond formation. This ingenious ester engages in a delicate tango with the amino group of another amino acid crafting a robust covalent connection. Its prowess in peptide synthesis makes it a coveted instrument in the realm of protein engineering and pharmaceutical evolution.

Protein Labelling: Delving into the mysteries of protein behavior, this versatile ester shines in the art of protein adornment with an array of tags and probes for meticulous scrutiny and analysis. By harmonizing with the primary amines in proteins, it orchestrates the elegant attachment of vibrant fluorescent dyes biotin or other alluring agents. This enchanting dance is essential for unraveling the intricacies of protein localization interactions and quantification amidst the tapestry of complex biological samples.

Antibody Conjugation: In the realm of immunochemistry, the esteemed Z-L-alanine-N-hydroxysuccinimide ester takes center stage guiding the divine union of antibodies with an assortment of enzymatic fluorescent or molecular partners. This sacred ritual is paramount for the birth of sensitive and specific immunoassays like the fabled ELISA and mesmerizing immunofluorescence. Through this alchemical process the detection prowess of antibodies is heightened bestowing upon mankind more accurate and reliable diagnostic

manifestations.

Bioconjugate Chemistry: Within the hallowed halls of bioconjugate chemistry, the esteemed ester acts as a masterful architect weaving biomolecules together in an elegant tapestry of unity. This noble endeavor gives rise to wondrous creations such as the mythical drug-antibody conjugates marrying therapeutic virtues with targeting finesse. Its noble contributions propel the evolution of targeted drug delivery systems and herald the age of precision medicine with resounding impact.

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. 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.

3. 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.