L-Prolinol
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L-Prolinol

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An intermediate in the synthesis of Physostigmine and Physostigmine derivative for Alzheimer's disease treatment.

Category
Amino Alcohol
Catalog number
BAT-000646
CAS number
23356-96-9
Molecular Formula
C5H11NO
Molecular Weight
101.2
L-Prolinol
IUPAC Name
[(2S)-pyrrolidin-2-yl]methanol
Synonyms
L-(+)-Prolinol; (2S)-2-Pyrrolidinemethanol; (+)-2-Pyrrolidinemethanol
Appearance
Yellow oil
Purity
≥ 99% (GC, HPLC)
Density
1.025 g/mL at 25 °C
Melting Point
72-78 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C5H11NO/c7-4-5-2-1-3-6-5/h5-7H,1-4H2/t5-/m0/s1
InChI Key
HVVNJUAVDAZWCB-YFKPBYRVSA-N
Canonical SMILES
C1CC(NC1)CO
1. Synthesis of large-pore zeolites from chiral structure-directing agents with two l-prolinol units
Luis Gómez-Hortigüela, Álvaro Mayoral, Haining Liu, Laura Sierra, Laura Vaquerizo, Cristina Mompeán, Joaquín Pérez-Pariente Dalton Trans. 2020 Jul 21;49(28):9618-9631. doi: 10.1039/d0dt01834a.
In this work, we perform an in-depth experimental and computational study about the structure-directing effect of two new chiral organic quaternary ammonium dications bearing two N-methyl-prolinol units linked by a xylene spacer in para or meta relative orientation, displaying four enantiopure stereogenic centers in (S) configuration. Synthesis results show that the para-xylene derivative is an efficient structure-directing agent, promoting the crystallization of ZSM-12 (in pure-silica composition), beta zeolite (as pure-silica, or in the presence of Al or Ge), and a mixture of polymorphs C, A and B of zeolite beta (in the presence of Ge). In contrast, the meta-xylene derivative showed a much poorer structure-directing activity, yielding only amorphous materials unless Ge is present in the gel, where beta and polymorph C (together with A and B) zeolites crystallized. Molecular simulations showed that the para-xylene dication displays a cylindrical shape suitable for confining in zeolite pores, while the meta-xylene derivative has an angular shape that shifts from the typical dimensions required for 12MR zeolite channels. Despite enantio-purity of the para-xylene dication with (S,S,S,S) configuration, no enrichment in polymorph A of the zeolite beta samples obtained was observed by Transmission Electron Microscopy. With the aid of molecular simulations, the failure in transferring chirality to the zeolite is explained by the loose fit of this SDA in the large-pores of zeolite beta, and a lack of close geometrical fit with the chiral element of polymorph A, as evidenced by the very similar interaction of the cation with the two enantiomorphic space groups of polymorph A. Nevertheless, the molecular-level knowledge gained in this work can provide insights for the future design of more efficient SDAs towards the synthesis of chiral zeolites.
2. Quatsomes Formulated with l-Prolinol-Derived Surfactants as Antibacterial Nanocarriers of (+)-Usnic Acid with Antioxidant Activity
Sara Battista, et al. ACS Appl Nano Mater. 2022 May 27;5(5):6140-6148. doi: 10.1021/acsanm.1c04365. Epub 2022 May 9.
The efficacy of the treatment of bacterial infection is seriously reduced because of antibiotic resistance; thus, therapeutic solutions against drug-resistant microbes are necessary. Nanoparticle-based solutions are particularly promising for meeting this challenge because they can offer intrinsic antimicrobial activity and sustained drug release at the target site. Herein, we present a newly developed nanovesicle system of the quatsome family, composed of l-prolinol-derived surfactants and cholesterol, which has noticeable antibacterial activity even on Gram-negative strains, demonstrating great potential for the treatment of bacterial infections. We optimized the vesicle stability and antibacterial activity by tuning the surfactant chain length and headgroup charge (cationic or zwitterionic) and show that these quatsomes can furthermore serve as nanocarriers of pharmaceutical actives, demonstrated here by the encapsulation of (+)-usnic acid, a natural substance with many pharmacological properties.
3. L-prolinol as a highly enantioselective catalyst for Michael addition of cyclohexanone to nitroolefins
Pei Juan Chua, Bin Tan, Xiaofei Zeng, Guofu Zhong Bioorg Med Chem Lett. 2009 Jul 15;19(14):3915-8. doi: 10.1016/j.bmcl.2009.03.076. Epub 2009 Mar 25.
Though many chiral amines such as l-proline and its derivatives have proven to be versatile catalysts in many reactions, L-prolinol was seldom used as organocatalyst for reactions. Herein, we report the first L-prolinol catalyzed asymmetric Michael addition of cyclohexanone to nitroolefins in the presence of benzoic acid to afford Michael adducts with high diastereoselectivities (87:13->99:1) and enantioselectivities (82-96%).
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