trans-4-Fluoro-L-proline
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trans-4-Fluoro-L-proline

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trans-4-Fluoro-L-proline, a derivative of proline, functions as a pivotal component in the intricate process of drug development within the realms of pharmacology and chemical research. Employed predominantly for the innovation and formulation of therapeutic agents targeting an extensive array of pathological conditions such as oncological malignancies and neurodegenerative dysfunctions.

Category
Cyclic Amino Acids
Catalog number
BAT-001661
CAS number
2507-61-1
Molecular Formula
C5H8FNO2
Molecular Weight
133.12
trans-4-Fluoro-L-proline
IUPAC Name
(2S,4R)-4-fluoropyrrolidine-2-carboxylic acid
Synonyms
trans-4-Fluoro-L-Pro-OH; L-Proline, 4-fluoro-, (4R)-; (4R)-4-Fluoro-L-proline; L-Proline, 4-fluoro-, trans-; Proline, 4-fluoro-, L-trans-; (2S,4R)-4-Fluoro-pyrrolidine-2-carboxylic acid; trans-4-Fluoropyrrolidine-2-carboxylic Acid; L-trans-4-Fluoroproline; trans-4-Fluoroproline
Appearance
White to Light Yellow Powder to Crystal
Purity
≥95%
Density
1.30±0.1 g/cm3
Melting Point
264°C
Boiling Point
265.1±40.0°C at 760 mmHg
Storage
Store at RT
InChI
InChI=1S/C5H8FNO2/c6-3-1-4(5(8)9)7-2-3/h3-4,7H,1-2H2,(H,8,9)/t3-,4+/m1/s1
InChI Key
ZIWHMENIDGOELV-DMTCNVIQSA-N
Canonical SMILES
C1C(CNC1C(=O)O)F
1. (1 R,2 S,4 r)-1,2,4-Tri-phenyl-cyclo-pentane-1,2-diol and (1 R,2 S,4 r)-4-(2-meth-oxy-phen-yl)-1,2-di-phenyl-cyclo-pentane-1,2-diol: application as initiators for ring-opening polymerization of ∊-caprolactone
Pavel D Komarov, Mikhail E Minyaev, Andrei V Churakov, Dmitrii M Roitershtein, Ilya E Nifant'ev Acta Crystallogr E Crystallogr Commun. 2019 Jun 21;75(Pt 7):1035-1040. doi: 10.1107/S2056989019008673. eCollection 2019 Jul 1.
Reductive cyclization of 1,3,5-triphenyl- and 3-(2-meth-oxy-phen-yl)-1,5-di-phenyl-pentane-1,5-diones by zinc in acetic acid medium leads to the formation of 1,2,4-tri-phenyl-cyclo-pentane-1,2-diol [1,2,4-Ph3C5H5-1,2-(OH)2, C23H22O2, (I)] and 4-(2-meth-oxy-phen-yl)-1,2-di-phenyl-cyclo-pentane-1,2-diol [4-(2-MeOC6H4)-1,2-Ph2C5H5-1,2-(OH)2, C24H24O3, (II)]. Their single crystals have been obtained by crystallization from a THF/hexane solvent mixture. Diols (I) and (II) crystallize in ortho-rhom-bic (Pbca) and triclinic (P ) space groups, respectively, at 150 K. Their asymmetric units comprise one [in the case of (I)] and three [in the case of (II)] crystallographically independent mol-ecules of the achiral (1R,2S,4r)-diol isomer. Each hydroxyl group is involved in one intra-molecular and one inter-molecular O-H⋯O hydrogen bond, forming one-dimensional chains. Compounds (I) and (II) have been used successfully as precatalyst activators for the ring-opening polymerization of ∊-caprolactone.
2. (1S*,2S*,4R*,5R*)-Cyclo-hexane-1,2,4,5-tetra-carb-oxy-lic acid
Akira Uchida, Masatoshi Hasegawa, Shinya Yamaguchi, Eiichiro Takezawa, Atsushi Ishikawa, Takashi Kagayama Acta Crystallogr Sect E Struct Rep Online. 2013 Dec 21;70(Pt 1):o75. doi: 10.1107/S1600536813033795. eCollection 2014 Jan 1.
The title compound, C10H12O8, a prospective raw material for colourless polyimides which are applied to electronic and microelectronic devices, lies about an inversion centre and the cyclo-hexane ring adopts a chair conformation. Two crystallographycally independent carb-oxy-lic acid groups on adjacent C atoms are in equatorial positions, resulting in a mutually trans conformation. In the crystal, O-H⋯O hydrogen bonds around an inversion centre and a threefold rotoinversion axis, respectively, form an inversion dimer with an R 2 (2)(8) motif and a trimer with an R 3 (3)(12) motif.
3. Design and Synthesis of a Series of l-trans-4-Substituted Prolines as Selective Antagonists for the Ionotropic Glutamate Receptors Including Functional and X-ray Crystallographic Studies of New Subtype Selective Kainic Acid Receptor Subtype 1 (GluK1) Antagonist (2S,4R)-4-(2-Carboxyphenoxy)pyrrolidine-2-carboxylic Acid
Niels Krogsgaard-Larsen, et al. J Med Chem. 2017 Jan 12;60(1):441-457. doi: 10.1021/acs.jmedchem.6b01516. Epub 2016 Dec 22.
Ionotropic glutamate receptor antagonists are valuable tool compounds for studies of neurological pathways in the central nervous system. On the basis of rational ligand design, a new class of selective antagonists, represented by (2S,4R)-4-(2-carboxyphenoxy)pyrrolidine-2-carboxylic acid (1b), for cloned homomeric kainic acid receptors subtype 1 (GluK1) was attained (Ki = 4 μM). In a functional assay, 1b displayed full antagonist activity with IC50 = 6 ± 2 μM. A crystal structure was obtained of 1b when bound in the ligand binding domain of GluK1. A domain opening of 13-14° was seen compared to the structure with glutamate, consistent with 1b being an antagonist. A structure-activity relationship study showed that the chemical nature of the tethering atom (C, O, or S) linking the pyrrolidine ring and the phenyl ring plays a key role in the receptor selectivity profile and that substituents on the phenyl ring are well accommodated by the GluK1 receptor.
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