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BOC-Amino Acids
Catalog number
CAS number
Molecular Formula
Molecular Weight
(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
Boc-L-Ala-OH; N-(tert-Butoxycarbonyl)-L-alanine
White to off-white powder
≥ 99.5% (Chiral HPLC)
1.2321 g/cm3(rough estimate)
Melting Point
78-85 °C
Boiling Point
324.46°C (rough estimate)
Store at 2-8 °C
InChI Key
Canonical SMILES
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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