Boc-3-(4'-pyridyl)-L-alanine
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Boc-3-(4'-pyridyl)-L-alanine

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Boc-3-(4'-pyridyl)-L-alanine is the protected form of L-Alanine, a non-essential amino acid that can be found naturally in the human body and is obtained by our diet.

Category
BOC-Amino Acids
Catalog number
BAT-007967
CAS number
37535-57-2
Molecular Formula
C13H18N2O4
Molecular Weight
266.29
Boc-3-(4'-pyridyl)-L-alanine
IUPAC Name
(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-pyridin-4-ylpropanoic acid
Synonyms
Boc-L-Ala(4'-pyridyl)-OH; Boc-(S)-2-amino-3-(4'-pyridyl)propanoic acid; Boc-L-4-Pyridylalanine; Boc-Ala(4-pyridyl)-OH; Boc-3-(4-pyridyl)-L-alanine; Boc-4-Pal-Oh; (S)-2-((tert-Butoxycarbonyl)amino)-3-(pyridin-4-yl)propanoic acid; N-(tert-butoxycarbonyl)-3-pyridin-4-yl-L-alanine; Boc-L-3-(4-pyridyl)-alanine
Appearance
White to off-white powder
Purity
≥ 99.5% (Chiral HPLC)
Density
1.200 g/cm3
Melting Point
224-232 °C
Boiling Point
454.3 °C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C13H18N2O4/c1-13(2,3)19-12(18)15-10(11(16)17)8-9-4-6-14-7-5-9/h4-7,10H,8H2,1-3H3,(H,15,18)(H,16,17)/t10-/m0/s1
InChI Key
FNYWDMKESUACOU-JTQLQIEISA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CC1=CC=NC=C1)C(=O)O

Boc-3-(4'-pyridyl)-L-alanine, a versatile chemical compound widely utilized in peptide synthesis and various biochemical applications, exhibits a diverse range of functions. Here are the key applications presented with a high degree of perplexity and burstiness:

Peptide Synthesis: Functioning as a crucial protective derivative in the intricate realm of peptide synthesis, Boc-3-(4'-pyridyl)-L-alanine plays a pivotal role in orchestrating the meticulous stepwise construction of peptides. By providing a shield for the amine group, it enables selective deprotection and precise coupling reactions, ultimately enhancing the efficiency and accuracy of peptide assembly. This sophisticated process streamlines the production of complex peptides with exceptional purity and structural integrity.

Drug Development: Positioned at the forefront of pharmaceutical innovation, Boc-3-(4'-pyridyl)-L-alanine stands as a cornerstone in the design and synthesis of peptide-based drug candidates. Its pyridyl group interacts adeptly with a diverse array of biological targets, facilitating the creation of peptides endowed with specific biological activities. This groundbreaking advancement propels the development of novel therapeutics for a wide spectrum of diseases ushering in a new era of precision medicine.

Protein Engineering: Within the dynamic realm of protein engineering, Boc-3-(4'-pyridyl)-L-alanine emerges as a key facilitator in introducing tailored modifications into proteins to unravel their complex structure-function relationships. By seamlessly integrating this compound into protein sequences, researchers can meticulously interrogate the repercussions of specific residue alterations on protein stability and activity. This foundational work is essential for crafting proteins with enhanced functionalities and novel capabilities driving innovation in biotechnology.

Molecular Probes: Harnessing the versatile nature of Boc-3-(4'-pyridyl)-L-alanine, researchers leverage its unique pyridyl group to craft sophisticated molecular probes for probing biochemical pathways and enzyme activities with unparalleled precision. This compound serves as a fundamental building block for developing fluorescent or affinity tags, enabling the creation of probes utilized in various analytical techniques such as fluorescence microscopy and mass spectrometry. These advanced tools empower detailed investigations into molecular processes unraveling the intricacies of biological systems with remarkable precision.

1.Temperature-Mediated Variations in Cellular Membrane Fatty Acid Composition of Staphylococcus aureus in Resistance to Pulsed Electric Fields.
Wang LH1, Wang MS1, Zeng XA2, Liu ZW1. Biochim Biophys Acta. 2016 May 4. pii: S0005-2736(16)30145-6. doi: 10.1016/j.bbamem.2016.05.003. [Epub ahead of print]
Effects of growth temperature on cell membrane fatty acid composition, fluidity and lethal and sublethal injury by pulsed electric fields (PEF) in Staphylococcus aureus ATCC 43300 (S. aureus) in the stationary phase were investigated. Analysis of the membrane fatty acids by gas chromatography-mass spectrometry (GC-MS) revealed that branched chain fatty acids (iso C14:0, iso C15:0, anteiso C15:0 and anteiso C17:0) and straight chain fatty acids (C12:0, C14:0, C16:0, C17:0 and C18:0) were primary constituents in the membrane. The S. aureus changed its membrane fatty acid composition and its overall fluidity when exposed to different temperatures. The PEF lethal and sublethal effects were assessed, and results suggested that the degree of inactivation depended on the cell membrane structure, electric field strength and treatment time. The PEF inactivation kinetics including lethal and sublethal injury fractions were fitted with non-linear Weibull distribution, suggesting that inactivation of the first log cycle of S.
2.Direct detection of circulating free DNA extracted from serum samples of breast cancer using locked nucleic acid molecular beacon.
Gui Z1, Wang Q2, Li J1, Zhu M1, Yu L1, Xun T1, Yan F3, Ju H4. Talanta. 2016 Jul 1;154:520-5. doi: 10.1016/j.talanta.2016.04.008. Epub 2016 Apr 7.
As an emerging noninvasive blood biomarker, circulating free DNA (cfDNA) can be utilized to assess diagnosis, progression and evaluate prognosis of cancer. However, cfDNAs are not "naked", they can be part of complexes, or are bound to the surface of the cells via proteins, which make the detection more challenging. Here, a simple method for the detection of Ubiquitin-like with PHD and ring finger domains 1 (UHRF1) DNA exacted from serum of breast cancer (BC) has been developed using a novel locked nucleic acid molecular beacon (LNA-MB). In order to enhance the stability and detection efficiency of the probe in biofluids, we design a shared-stem molecular beacon containing a 27-mer loop and a 4-mer stem with DNA/LNA alternating bases. The fluorescence is released in the presence of target. The detection procedure is simple and can be completed within 1h. This method shows a sensitive response to UHRF1 DNA with a dynamic range of 3 orders of magnitude.
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