Name: (2S,4R)-Fmoc-4-azido-pyrrolidine-2-carboxylic acid
Brand: BOC Sciences
Rating: 5 (1 reviews)

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Synonyms

Fmoc-(4R)-azido-L-Proline; Fmoc-(2S,4R)-4-azidoproline; (2S,4R)-4-Azido-1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidine-2-carboxylic acid

IUPAC Name

(2S,4R)-4-azido-1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidine-2-carboxylic acid

Canonical SMILES

C1C(CN(C1C(=O)O)C(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)N=[N+]=[N-]

InChI

InChI=1S/C20H18N4O4/c21-23-22-12-9-18(19(25)26)24(10-12)20(27)28-11-17-15-7-3-1-5-13(15)14-6-2-4-8-16(14)17/h1-8,12,17-18H,9-11H2,(H,25,26)/t12-,18+/m1/s1

InChIKey

HOPXMBBEYJTPNX-XIKOKIGWSA-N

Melting Point

55-58°C

Appearance

White to off-white crystalline powder

Storage

Store at 2-8 °C

(2S,4R)-Fmoc-4-azido-pyrrolidine-2-carboxylic acid, a synthetic compound commonly employed in peptide and protein chemistry, offers a multitude of applications. Here are four key applications presented with high perplexity and burstiness:

Peptide Synthesis: Serving as a foundational element in solid-phase peptide synthesis, (2S,4R)-Fmoc-4-azido-pyrrolidine-2-carboxylic acid plays a vital role in incorporating azido functionalities into peptides. This strategic maneuver sets the stage for subsequent modifications through click chemistry, underpinning the creation of intricate peptide structures and conjugates with unparalleled complexity and precision.

Protein Labeling: Within the realm of protein chemistry, this compound serves as a catalyst for introducing azido groups that enable precise site-specific labeling of proteins. The reactive azide groups engage in click chemistry reactions with diverse alkyne-containing molecules, facilitating the attachment of probes, tags, or other functional entities. Such targeted labeling methodologies are indispensable for delving into protein dynamics, interactions, and subcellular localization with unprecedented detail and clarity.

Bioconjugation: (2S,4R)-Fmoc-4-azido-pyrrolidine-2-carboxylic acid emerges as a cornerstone in the realm of bioconjugation, where peptides or proteins are seamlessly linked to other biomolecules or surfaces. The versatile azido group serves as a dynamic conduit for molecular attachment via Staudinger ligation or azide-alkyne cycloaddition, shaping the landscape of targeted drug delivery systems, diagnostic tools, and cutting-edge biosensors with intricate and versatile capabilities.

Chemical Biology: In the interdisciplinary domain of chemical biology, this compound stands as an invaluable tool for dissecting protein function and cellular processes. By integrating azido groups into biomolecules, researchers can harness bioorthogonal reactions to intricately probe and manipulate biological systems without disrupting native cellular functions. This strategic approach empowers in-depth investigations into cellular pathways and catalyzes the development of novel therapeutic modalities, pushing the boundaries of scientific exploration and innovation.

1. 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.

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.