267230-44-4

Basic information

• Product Name: (3R,4S)-1-Boc-4-Fmoc-amino-3-pyrrolidinecarboxylic acid
• Synonyms: (3R,4S)-1-Boc-4-Fmoc-amino-3-pyrrolidinecarboxylic acid;(3R,4S)-4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-1-(tert-butoxycarbonyl)pyrrolidine-3-carbox;(3R,4S)-1-[(tert-butoxy)carbonyl]-4-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}pyrrolidine-3-carboxylic acid;(3R,4S)-4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-1-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid;(3R,4S)-4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-1-(tert-butoxycarbonyl)pyrrolidine-3-car;APC (3R,4S)-4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-1-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid
• CAS NO: 267230-44-4
• Molecular Formula: C₂₅H₂₈N₂O₆
• Molecular Weight: 452.51
• Product Categories: pharmacetical
• Mol File: 267230-44-4.mol

Chemical Properties

• Boiling Point: 650.2°Cat760mmHg
• Flash Point: 347°C
• Appearance: /
• Density: 1.33g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.627
• Storage Temp.: 2-8°C
• PKA: 4.17±0.40(Predicted)
• CAS DataBase Reference: (3R,4S)-1-Boc-4-Fmoc-amino-3-pyrrolidinecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4S)-1-Boc-4-Fmoc-amino-3-pyrrolidinecarboxylic acid(267230-44-4)
• EPA Substance Registry System: (3R,4S)-1-Boc-4-Fmoc-amino-3-pyrrolidinecarboxylic acid(267230-44-4)

Safety Data

• Hazardous Substances Data: 267230-44-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(3R,4S)-1-Boc-4-Fmoc-amino-3-pyrrolidinecarboxylic acid is used as a building block for the synthesis of peptides and pharmaceuticals due to its protective groups and versatile chemical structure. (3R,4S)-1-Boc-4-Fmoc-amino-3-pyrrolidinecarboxylic acid's stereochemistry allows for specific interactions in biological systems, which is essential for the development of targeted therapeutics.
Used in Organic Synthesis:
In the field of organic synthesis, (3R,4S)-1-Boc-4-Fmoc-amino-3-pyrrolidinecarboxylic acid is used as an intermediate for the preparation of heterocyclic compounds and other complex organic molecules. Its unique structure and functional groups enable the creation of diverse chemical entities with potential applications in various industries.
Used in Research and Development:
(3R,4S)-1-Boc-4-Fmoc-amino-3-pyrrolidinecarboxylic acid serves as a valuable tool in research and development for the creation of novel chemical structures and compounds. Its stereochemistry and functional groups allow scientists to explore new avenues in chemical synthesis and potentially discover new pharmaceuticals or materials with specific properties.

InChI:InChI=1/C25H28N2O6/c1-25(2,3)33-24(31)27-12-19(22(28)29)21(13-27)26-23(30)32-14-20-17-10-6-4-8-15(17)16-9-5-7-11-18(16)20/h4-11,19-21H,12-14H2,1-3H3,(H,26,30)(H,28,29)/t19-,21-/m1/s1

Upstream product

• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 369623-85-8 (3R,4S)-4-Amino-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 
• 267230-43-3 (3R,4S)-4-Benzyloxycarbonylamino-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 
• 388109-45-3 (3R,4S)-4-[(R)-1-phenyl-ethylamino]-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 
• 346610-81-9 (3S,4R)-1-(N-tert-butoxycarbonyl)-3-[(1'R)-phenylethylamino]pyrrolidine-4-carboxylic acid ethyl ester hydrochloride 
• 267230-42-2 (3R,4S)-4-Benzyloxycarbonylamino-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester 

Downstream Products

• 1345261-76-8 (3S,4R)-1-(N-tert-butoxycarbonyl)-3-(9H-fluoren-9-yl-methoxycarbonylamino)pyrrolidine-4-carboxylic acid pentafluorophenyl ester 

Relevant articles and documents

3-Aminopyrrolidine-4-carboxylic acid as versatile handle for internal labeling of pyrrolidinyl PNA

Conformationally restricted pyrrolidinyl PNAs with an a/b-dipeptide backbone consisting of a nucleobase- modified proline and a cyclic five-membered amino acid spacer such as (1S,2S)-2-aminocyclopentanecarboxylic acid (ACPC) (acpcPNA) can form very stable hybrids with DNA with high Watson-Crick base pairing specificity. This work aims to explore the effect of incorporating 3-aminopyrrolidine-4-carboxylic acid (APC), whi h is isosteric to the ACPC spacer, into the acpcPNA. It is expected that the modification should not negatively affect the DNA binding properties, and that the additional nitrogen atom in the APC should provide a handle for internal modification. Orthogonally-protected (N3-Fmoc/N1-Boc and N3-Fmoc/N1-Tfa) APC monomers have been successfully synthesized and incorporated into the acpcPNA by Fmoc-solid-phase peptide synthesis. Tm, UV and CD spectroscopy confirmed that the (3R,4S)-APC could substitute the (1S,2S)-ACPC spacer in the acpcPNA with only slightly decreasing the stability of the hybrids formed between the modified acpc/apcPNA and DNA. In contrast, the (3S,4R) enantiomer of APC caused substantial destabilization of the hybrids. Furthermore, a successful on-solid-support internal labeling of the acpc/apcPNA via amide bond formation between pyrene-1-carboxylic acid or 4-(pyrene-1-yl) butyric acid and the pyrrolidine nitrogen atom of the APC spacer has been demonstrated. Fluorescence properties of the pyrene-labeled acpc/apcPNAs are sensitive to their hybridization states and can readily distinguish between complementary and single-mismatched DNA targets.