Boc-L-alaninol
Need Assistance?
  • US & Canada:
    +
  • UK: +

Boc-L-alaninol

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

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 °C
Boiling Point
276.4 °C at 760 mmHg
Storage
Store at 2-8 °C
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

Boc-L-alaninol, a versatile chiral auxiliary and protecting group prevalent in organic synthesis particularly in peptide chemistry, finds diverse applications. Here are four the applications presented with elevated perplexity and burstiness:

Peptide Synthesis: Playing a pivotal role in peptide synthesis, Boc-L-alaninol acts as a safeguarding entity for the amino group shielding it from undesired reactions throughout the synthetic processes. Upon the completion of desired transformations, the Boc group can be selectively removed under acidic conditions unveiling the liberated amine in all its chemical glory.

Chiral Resolution: Delving into the realm of chiral resolution, Boc-L-alaninol emerges as a crucial player in obtaining enantiomerically pure compounds. This compound functions as a resolving agent engaging in the formation of diastereomeric salts or complexes with racemic mixtures setting the stage for their separation through conventional purification methods ultimately yielding pure enantiomers.

Asymmetric Synthesis: Stepping into the domain of asymmetric synthesis, Boc-L-alaninol assumes the role of a chiral auxiliary orchestrating enantioselectivity in chemical reactions with finesse. By strategically attaching it to substrates this compound steers the formation of chiral centers in a predictable fashion essential for the synthesis of stereoselective compounds that hold profound significance in the pharmaceutical landscape.

Structural Component in Medicinal Chemistry: Embracing its identity as a structural cornerstone in medicinal chemistry, Boc-L-alaninol serves as a fundamental building block for the design and synthesis of bioactive molecules. Its inherent chirality and adeptness at safeguarding amino groups render it ideal for crafting intricate molecular architectures with these derivatives assuming pivotal roles in the intricate dance of drug discovery and development.

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.
Online Inquiry
Verification code
Inquiry Basket