Boc-L-alaninol
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Boc-L-alaninol

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Boc-L-alaninol (CAS# 79069-13-9) is a useful research chemical.

Category
Amino Alcohol
Catalog number
BAT-000360
CAS number
79069-13-9
Molecular Formula
C8H17NO3
Molecular Weight
175.20
Boc-L-alaninol
IUPAC Name
tert-butyl N-[(2S)-1-hydroxypropan-2-yl]carbamate
Synonyms
Boc-L-Ala-ol; N-Boc-L-alaninol; N-tert-Butoxycarbonyl-L-alaninol; tert-butyl N-[(2S)-1-hydroxypropan-2-yl]carbamate
Appearance
Off-white or white powder
Purity
≥ 99 % (GC)
Density
1.025 g/cm3
Melting Point
53-58 ℃
Boiling Point
276.4 ℃ at 760 mmHg
Storage
Store at 2-8 ℃
InChI
InChI=1S/C8H17NO3/c1-6(5-10)9-7(11)12-8(2,3)4/h6,10H,5H2,1-4H3,(H,9,11)/t6-/m0/s1
InChI Key
PDAFIZPRSXHMCO-LURJTMIESA-N
Canonical SMILES
CC(CO)NC(=O)OC(C)(C)C
1. 4-Vinylproline
Ramakotaiah Mulamreddy, N D Prasad Atmuri, William D Lubell J Org Chem. 2018 Nov 2;83(21):13580-13586. doi: 10.1021/acs.joc.8b02177. Epub 2018 Oct 11.
Enantiomerically pure 4-vinylproline (Vyp) was synthesized by a five-step approach from N-(Boc)iodo-alanine (2) featuring copper-catalyzed SN2' substitution of the corresponding zincate onto ( Z)-1,4-dichlorobut-2-ene to prepare methyl 2- N-(Boc)amino-4-(chloromethyl)hexenoate (3). Intra- and intermolecular displacement of the chloride provided respectively Vyp and methyl 2- N-(Boc)amino-4-(azidomethyl)hexenoate (7) suitable for the synthesis of constrained peptide analogs.
2. Synthesis and crystal structures of Boc-L-Asn-L-Pro-OBzl.CH3OH and dehydration side product, Boc-beta-cyano-L-alanine-L-Pro-OBzl
A N Stroup, L B Cole, M M Dhingra, L M Gierasch Int J Pept Protein Res. 1990 Dec;36(6):531-7. doi: 10.1111/j.1399-3011.1990.tb00992.x.
Boc-L-Asn-L-Pro-OBzl: C21H29O6N3.CH3OH, Mr = 419.48 + CH3 OH, monoclinic, P2(1), a = 10.049(1), b = 10.399(2), c = 11.702(1) A, beta = 92.50(1)degrees, V = 1221.7(3) A3, dx = 1.14 g.cm-3, Z = 2, CuK alpha (lambda = 1.54178 A), F(000) = 484 (with solvent), 23 degrees, unique reflections (I greater than 3 sigma(I)) = 1745, R = 0.043, Rw = 0.062, S = 1.66. Boc-beta-cyano-L-alanine-L-Pro-OBzl: C21H27O5N3, Mr = 401.46, orthorhombic, P2(1)2(1)2(1), a = 15.741(3), b = 21.060(3), c = 6.496(3) A, V = 2153(1) A3, dx = 1.24 g.cm-3, Z = 4, CuK alpha (lambda = 1.54178 A), F(000) = 856, 23 degrees, unique reflections (I greater than 3 sigma(I)) = 1573, R = 0.055, Rw = 0.078, S = 1.86. The tert.-butyloxycarbonyl (Boc) protected dipeptide benzyl ester (OBzl), Boc-L-Asn-L-Pro-OBzl, prepared from a mixed anhydride reaction using isobutylchloroformate, Boc-L-asparagine, and HCl.L-proline-OBzl, crystallized with one methanol per asymmetric unit in an extended conformation with the Asn-Pro peptide bond trans. Intermolecular hydrogen bonding occurs between the methanol and the Asn side chain and between the peptide backbone and the Asn side chain. A minor impurity due to the dehydration of the Asn side chain to a beta-CNala crystallized with a similar extended conformation and a single intermolecular hydrogen bond.
3. 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.
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