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A chiral building block for the synthesis of novel fluorescent chemosensors for amino acid.

Amino Alcohol
Catalog number
CAS number
Molecular Formula
Molecular Weight
H-D-Phg-ol; (R)-2-Amino-2-phenylethanol; (R)-(-)-2-Phenylglycinol; (R)-2-Phenylglycinol
White to pale yellow crystalline solid
≥ 99 %
1.104 g/cm3
Melting Point
72-82 ℃
Boiling Point
261 ℃ at 760 mmHg
Store at 2-8 ℃
InChI Key
Canonical SMILES
1. Structure of a Dimeric BINOL-Imine-Zn(II) Complex and Its Role in Enantioselective Fluorescent Recognition
Kai Guo, Ping Wang, Wanli Tan, Yan Li, Xiaowei Gao, Qin Wang, Lin Pu Inorg Chem. 2020 Dec 21;59(24):17992-17998. doi: 10.1021/acs.inorgchem.0c02330. Epub 2020 Nov 2.
A pyridine containing BINOL-based aldehyde (S)- or (R)-4 is found to show highly enantioselective fluorescent response toward phenylglycinol in the presence of Zn2+. A chirality matched dimeric BINOL-imine-Zn(II) complex is isolated from the reaction of (S)-4 with l-phenylglycinol and Zn2+ whose structure is established by X-ray analysis. Comparison of the structure of this SS-complex with a molecular modeling structure of the chirality mismatched SR-complex generated from the reaction of (S)-4 with d-phenylglycinol has provided important insight into the origin of the observed highly enantioselective fluorescent response. It is found that the solvent-accessible surface area of the chirality-matched SS-complex is much smaller than that of the chirality mismatched SR-complex, which gives the more tightly packed and structurally rigid SS-complex with greatly enhanced fluorescence.
2. D-phenylglycinol-derived non-covalent factor Xa inhibitors: effect of non-peptidic S4 linkage elements on affinity and anticoagulant activity
Valentine J Klimkowski, et al. Bioorg Med Chem Lett. 2007 Nov 1;17(21):5801-5. doi: 10.1016/j.bmcl.2007.08.051. Epub 2007 Aug 28.
Analogs to a series of D-phenylglycinamide-derived factor Xa inhibitors were discovered. It was found that the S4 amide linkage can be replaced with an ether linkage to reduce the peptide character of the molecules and that this substitution leads to an increase in binding affinity that is not predicted based on modeling. Inhibitors which incorporate ether, amino, or alkyl S4 linkage motifs exhibit similar levels of binding affinity and also demonstrate potent in vitro functional activity, however, binding affinity in this series is strongly dependent on the nature of the S1 binding element.
3. Simultaneous Construction of Planar and Central Chiralities as Well as Unprecedented Axial Chirality on and around a Ferrocene Backbone
Hongjie Li, Peijing Jia, Naixin Qian, Shasha Li, Peng Jiao J Org Chem. 2019 Mar 1;84(5):2817-2828. doi: 10.1021/acs.joc.8b03221. Epub 2019 Feb 11.
Simultaneous generation of planar, central and axial chiralities on and around a ferrocene backbone via a d-phenylglycinol-induced intramolecular iminium cyclization was disclosed, which is rare and differs from known methods. A series of chiral spiro[cyclopentadienyl-1,2,3,3a-tetrahydropentalenyliron(II)-1,2'-pyrrolidine] derivatives were prepared acording to the new method, and their structures were characterized unambiguously. The axial chirality caused by the ferrocene backbone and the rigid spiral structure was verified by NOESY and variable-temperature NMR experiments and single-crystal XRD analyses. Mechanism for the stereoselective iminium cyclization reaction was suggested, which was influenced by steric hindrance and hydrogen bonding.

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