Boc-L-alanine
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Boc-L-alanine

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Category
BOC-Amino Acids
Catalog number
BAT-002748
CAS number
15761-38-3
Molecular Formula
C8H15NO4
Molecular Weight
189.20
Boc-L-alanine
IUPAC Name
(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
Synonyms
Boc-L-Ala-OH; N-(tert-Butoxycarbonyl)-L-alanine
Appearance
White to off-white powder
Purity
≥ 99.5% (Chiral HPLC)
Density
1.2321 g/cm3(rough estimate)
Melting Point
78-85 °C
Boiling Point
324.46°C (rough estimate)
Storage
Store at 2-8 °C
InChI
InChI=1S/C8H15NO4/c1-5(6(10)11)9-7(12)13-8(2,3)4/h5H,1-4H3,(H,9,12)(H,10,11)/t5-/m0/s1
InChI Key
QVHJQCGUWFKTSE-YFKPBYRVSA-N
Canonical SMILES
CC(C(=O)O)NC(=O)OC(C)(C)C

Boc-L-alanine, a protected amino acid widely employed in peptide synthesis and medicinal chemistry, offers a multitude of applications. Here are the key applications presented with high perplexity and burstiness:

Peptide Synthesis: Serving as a fundamental building block in peptide and protein synthesis, Boc-L-alanine plays a crucial role. The Boc (tert-butoxycarbonyl) group shields the amino group during coupling reactions mitigating undesired side reactions. Post-synthesis the Boc group can be acidically removed to yield the desired peptide showcasing the intricacies of peptide construction.

Drug Development: In the realm of medicinal chemistry, Boc-L-alanine plays a pivotal role in designing and synthesizing prodrugs and novel therapeutics. Integration of Boc-L-alanine into drug molecules enhances pharmacokinetic properties including stability and solubility. This augmentation boosts the drug's bioavailability and therapeutic effectiveness unveiling the complexity of drug optimization.

Biochemical Research: Delving into enzyme mechanisms and protein structure-function relationships, Boc-L-alanine proves indispensable. By introducing this protected amino acid into peptide substrates, scientists delve into enzyme kinetics and binding interactions unveiling the intricate molecular dance crucial for developing enzyme inhibitors and therapeutic targets.

Materials Science: Foraying into materials science, Boc-L-alanine contributes to the creation of biomaterials and coatings with tailored functionalities. Its incorporation into polymeric materials imparts biocompatibility and controlled release attributes lending versatility to medical devices drug delivery systems and tissue engineering applications. This innovative application highlights the diverse potential of Boc-L-alanine in pushing the boundaries of materials science.

1. 5- O-( N-Boc-l-Alanine)-Renieramycin T Induces Cancer Stem Cell Apoptosis via Targeting Akt Signaling
Darinthip Suksamai, et al. Mar Drugs. 2022 Mar 29;20(4):235. doi: 10.3390/md20040235.
Cancer stem cells (CSCs) drive aggressiveness and metastasis by utilizing stem cell-related signals. In this study, 5-O-(N-Boc-l-alanine)-renieramycin T (OBA-RT) was demonstrated to suppress CSC signals and induce apoptosis. OBA-RT exerted cytotoxic effects with a half-maximal inhibitory concentration of approximately 7 µM and mediated apoptosis as detected by annexin V/propidium iodide using flow cytometry and nuclear staining assays. Mechanistically, OBA-RT exerted dual roles, activating p53-dependent apoptosis and concomitantly suppressing CSC signals. A p53-dependent pathway was indicated by the induction of p53 and the depletion of anti-apoptotic Myeloid leukemia 1 (Mcl-1) and B-cell lymphoma 2 (Bcl-2) proteins. Cleaved poly (ADP-ribose) polymerase (Cleaved-PARP) was detected in OBA-RT-treated cells. Interestingly, OBA-RT exerted strong CSC-suppressing activity, reducing the ability to form tumor spheroids. In addition, OBA-RT could induce apoptosis in CSC-rich populations and tumor spheroid collapse. CSC markers, including prominin-1 (CD133), Octamer-binding transcription factor 4 (Oct4), and Nanog Homeobox (Nanog), were notably decreased after OBA-RT treatment. Upstream CSCs regulating active Akt and c-Myc were significantly decreased; indicating that Akt may be a potential target of action. Computational molecular modeling revealed a high-affinity interaction between OBA-RT and an Akt molecule. This study has revealed a novel CSC inhibitory effect of OBA-RT via Akt inhibition, which may improve cancer therapy.
2. Facile synthesis of multiamino vinyl poly(amino acid)s for promising bioapplications
Haiyan Sun, Chao Gao Biomacromolecules. 2010 Dec 13;11(12):3609-16. doi: 10.1021/bm101060m. Epub 2010 Nov 29.
We presented a general and facile strategy to prepare biocompatible multiamino polymers. Series of new monomers were synthesized by esterification of 2-hydroxyethyl methacrylate (HEMA) and Boc-amino acids, such as Boc-l-phenylalanine, Boc-glycine, Boc-l-alanine, Boc-l-valine, and Boc-l-lysine. Subsequent vinyl polymerization of monomers gave rise to vinyl poly(amino acid)s with a side primary amino group at each unit if deprotected. Both atom transfer radical polymerization (ATRP) and conventional free radical polymerization (FRP) were employed to prepare the multiamino polymers. A well controlled effect upon molecular weight with the standard first-order kinetics was achieved in cases of ATRP, and high molecular weight polymers were obtained via FRP. MTT assay showed that cell survival rates for the multiamino polymers were almost maintained above 90% and that their cytotoxicities were much lower than that of linear PEI (PEI 25000). Zeta potential measurements demonstrated that the vinyl poly(amino acid)s are electropositive, and AFM measurements showed that the vinyl poly(amino acid)s could tightly condense DNA into granular structures at a suitable concentration. The combination of facile availability, controlled productivity, low cytotoxicity and strong binding ability with DNA promises the great potential of the novel multiamino polymers in bioapplications.
3. Synthesis of isotopically labeled versions of L-MTP-PE (mifamurtide) and MDP
Yuexian Li, Mihaela Plesescu, Shimoga R Prakash J Labelled Comp Radiopharm. 2013 Jul-Aug;56(9-10):475-9. doi: 10.1002/jlcr.3078. Epub 2013 Jul 9.
L-MTP-PE (1), an immunomodulator and its metabolite MDP (4) were synthesized from labeled l-alanine and its protected derivative, respectively. The key intermediate product for the labeled L-MTP-PE synthesis, [(13) C3 ,D4 ]-alanyl-cephalin (2A), was synthesized from [(13) C3 ,D4 ]-l-alanine (3A) in three steps. The key intermediate product for labeled MDP synthesis, amine 11, was prepared from [(13) C3 ,(15) N]-Boc-l-alanine (5A) in two steps.
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