346610-79-5

Basic information

• Product Name: (3S,4R)-1-[(tert-butoxy)carbonyl]-4-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}pyrrolidine-3-carboxylic acid
• Synonyms: (3S,4R)-1-[(tert-butoxy)carbonyl]-4-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}pyrrolidine-3-carboxylic acid;(3S,4R)-1-Boc-4-Fmoc-amino-3-pyrrolidinecarboxylic acid
• CAS NO: 346610-79-5
• Molecular Formula: C₂₅H₂₈N₂O₆
• Molecular Weight: 452.51
• Mol File: 346610-79-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (3S,4R)-1-[(tert-butoxy)carbonyl]-4-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}pyrrolidine-3-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4R)-1-[(tert-butoxy)carbonyl]-4-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}pyrrolidine-3-carboxylic acid(346610-79-5)
• EPA Substance Registry System: (3S,4R)-1-[(tert-butoxy)carbonyl]-4-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}pyrrolidine-3-carboxylic acid(346610-79-5)

Safety Data

• Hazardous Substances Data: 346610-79-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
(3S,4R)-1-[(tert-butoxy)carbonyl]-4-[(9H-fluoren-9-ylmethoxy)carbonyl]aminopyrrolidine-3-carboxylic acid is used as a building block in the synthesis of peptide-based pharmaceuticals. Its protecting groups facilitate the controlled formation of peptide bonds, which is crucial for the development of new drugs with specific therapeutic properties.
Used in Organic Chemistry:
In the field of organic chemistry, (3S,4R)-1-[(tert-butoxy)carbonyl]-4-[(9H-fluoren-9-ylmethoxy)carbonyl]aminopyrrolidine-3-carboxylic acid serves as a versatile intermediate for the synthesis of various organic compounds. Its unique reactivity and protecting groups allow for the creation of complex molecules with potential applications in material science, agrochemicals, and other industries.

Upstream product

• 346610-81-9 (3R,4S)-1-(N-tert-butoxycarbonyl)-3-[(1'S)-phenylethylamino]pyrrolidine-4-carboxylic acid ethyl ester hydrochloride 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 369623-85-8 4-amino-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 

Downstream Products

• 1345261-66-6 (3R,4S)-1-(N-tert-butoxycarbonyl)-3-(9H-fluoren-9-ylmethoxycarbonylamino)pyrrolidine-4-carboxylic acid pentafluorophenyl ester 
• 1345261-68-8 (3R,4S)-1-(2,2,2-trifluoroacetyl)-3-(9H-fluoren-9-ylmethoxycarbonylamino)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.