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Application Area

N-β-Methyl-β-alanine t-butyl ester

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

Category

Other Unnatural Amino Acids

Catalog number

BAT-004787

CAS number

143707-72-6

Molecular Formula

C8H17NO2

Molecular Weight

159.23

IUPAC Name

tert-butyl 3-(methylamino)propanoate

Synonyms

H-β-MeAla-OtBu; H-MeGly-(C#CH2)OtBu; 3-(Methylamino)propanoic acid t-butyl ester

Density

0.920±0.06 g/cm3(Predicted)

Boiling Point

203.7±23.0 °C(Predicted)

Storage

Store at 2-8°C (under N2)

InChI

InChI=1S/C8H17NO2/c1-8(2,3)11-7(10)5-6-9-4/h9H,5-6H2,1-4H3

InChI Key

QFMOPRNLDIPINY-UHFFFAOYSA-N

Canonical SMILES

CC(C)(C)OC(=O)CCNC

N-β-Methyl-β-alanine t-butyl ester, a versatile chemical compound, finds extensive applications across scientific and industrial domains. Here are the key applications presented with a high degree of perplexity and burstiness:

Synthesis of Peptide Mimetics: Playing a pivotal role in peptide mimetics synthesis, N-β-Methyl-β-alanine t-butyl ester contributes to the creation of molecules that imitate peptides' structure and function. These mimetics play a crucial role in developing drugs that target specific proteins in the human body. By incorporating N-β-Methyl-β-alanine t-butyl ester, chemists can elevate the stability and bioavailability of these therapeutic agents, fostering advancements in pharmaceutical interventions.

Pharmaceutical Intermediate: Positioned as a strategic intermediate in the pharmaceutical landscape, N-β-Methyl-β-alanine t-butyl ester plays a significant role in synthesizing various active pharmaceutical ingredients (APIs). Its unique chemical characteristics make it a valuable cornerstone for constructing intricate organic molecules, streamlining the production of medications, and propelling progress in medical treatments.

Chemical Research: Within the realm of chemical research, N-β-Methyl-β-alanine t-butyl ester assumes the role of a reagent for investigating reaction mechanisms and pioneering new synthetic strategies. Its distinctive molecular structure renders it a captivating subject for exploration in organic chemistry. Through probing its reactivity and interactions, researchers can unearth novel reactions and potentially craft innovative compounds with practical utility, reshaping the landscape of chemical discovery.

Polymer Science: N-β-Methyl-β-alanine t-butyl ester emerges as a key player in the design and synthesis of avant-garde polymers boasting unique properties. These polymers find application across diverse domains, including materials science, drug delivery systems, and biocompatible devices. By integrating this compound, scientists can fabricate materials characterized by heightened mechanical strength, stability, and distinctive functional attributes, paving the way for cutting-edge material innovations.

1. Controlled Synthesis of Polyphosphazenes with Chain-Capping Agents

Krzysztof Matyjaszewski, Robert A Montague Molecules. 2021 Jan 10;26(2):322. doi: 10.3390/molecules26020322.

N-alkyl phosphoranimines were synthesized via the Staudinger reaction of four different alkyl azides with tris(2,2,2-trifluoroethyl) phosphite. N-adamantyl, N-benzyl, N-t-butyl, and N-trityl phosphoranimines were thoroughly characterized and evaluated as chain-capping compounds in the anionic polymerization of P-tris(2,2,2-trifluoroethoxy)-N-trimethylsilyl phosphoranimine monomer. All four compounds reacted with the active chain ends in a bulk polymerization, and the alkyl end groups were identified by 1H-NMR spectroscopy. These compounds effectively controlled the molecular weight of the resulting polyphosphazenes. The chain transfer constants for the monomer and N-benzyl phosphoranimine were determined using Mayo equation.

2. Shear Stress and VE-Cadherin

Vincenza Caolo, Hanna M Peacock, Bahar Kasaai, Geertje Swennen, Emma Gordon, Lena Claesson-Welsh, Mark J Post, Peter Verhamme, Elizabeth A V Jones Arterioscler Thromb Vasc Biol. 2018 Sep;38(9):2174-2183. doi: 10.1161/ATVBAHA.118.310823.

Objective- Vascular fusion represents an important mechanism of vessel enlargement during development; however, its significance in postnatal vessel enlargement is still unknown. During fusion, 2 adjoining vessels merge to share 1 larger lumen. The aim of this research was to identify the molecular mechanism responsible for vascular fusion. Approach and Results- We previously showed that both low shear stress and DAPT ( N-[ N-(3,5-difluorophenacetyl)-L-alanyl]- S-phenylglycine t-butyl ester) treatment in the embryo result in a hyperfused vascular plexus and that increasing shear stress levels could prevent DAPT-induced fusion. We, therefore, investigated vascular endothelial-cadherin (VEC) phosphorylation because this is a common downstream target of low shear stress and DAPT treatment. VEC phosphorylation increases after DAPT treatment and decreased shear stress. The increased phosphorylation occurred independent of the cleavage of the Notch intracellular domain. Increasing shear stress rescues hyperfusion by DAPT treatment by causing the association of the phosphatase vascular endothelial-protein tyrosine phosphatase with VEC, counteracting VEC phosphorylation. Finally, Src (proto-oncogene tyrosine-protein kinase Src) inhibition prevents VEC phosphorylation in endothelial cells and can rescue hyperfusion induced by low shear stress and DAPT treatment. Moesin, a VEC target that was previously reported to mediate endothelial cell rearrangement during lumenization, relocalizes to cell membranes in vascular beds undergoing hyperfusion. Conclusions- This study provides the first evidence that VEC phosphorylation, induced by DAPT treatment and low shear stress, is involved in the process of fusion during vascular remodeling.

3. Total Synthesis of (+)-Trachyspic Acid 19- n- Butyl Ester

Alex A Rafaniello, Mark A Rizzacasa Org Lett. 2020 Mar 6;22(5):1972-1975. doi: 10.1021/acs.orglett.0c00319. Epub 2020 Feb 17.

The first total synthesis of the alkyl citrate trachyspic acid 19-n-butyl ester (1) is described. A formal [2 + 2]-cycloaddition of the silylketene acetal derived from lactone 6 with di-n-butylacetylene dicarboxylate 7 provided the cyclobutene diester 5 with a dr >20:1. Acid-mediated rearrangement of 5 followed by lactone ring-opening and ester protecting group manipulation eventually provided orthogonally protected aldehyde 3. A Nozaki-Hiyama-Kishi coupling between 3 and vinyl iodide 4 followed by oxidation of the resultant allylic alcohol gave enone 16, which was converted into the triester 17 (dr 6:1) by a spirocyclization/oxidative cleavage/elimination sequence. Removal of the t-butyl esters then afforded trachyspic acid 19-n-butyl ester (1).