346610-81-9

Basic information

• Product Name: 1,3-Pyrrolidinedicarboxylic acid, 4-[[(1R)-1-phenylethyl]aMino]-, 1-(1,1-diMethylethyl) 3-ethyl ester, Monohydrochloride, (3S,4R)- (9CI)
• Synonyms: 1,3-Pyrrolidinedicarboxylic acid, 4-[[(1R)-1-phenylethyl]aMino]-, 1-(1,1-diMethylethyl) 3-ethyl ester, Monohydrochloride, (3S,4R)- (9CI);(3S,4R)-1-tert-butyl 3-ethyl 4-(((R)-1-phenylethyl)amino)pyrrolidine-1,3-dicarboxylate hydrochloride
• CAS NO: 346610-81-9
• Molecular Formula: C20H31ClN2O4
• Molecular Weight: 398.92414
• Mol File: 346610-81-9.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,3-Pyrrolidinedicarboxylic acid, 4-[[(1R)-1-phenylethyl]aMino]-, 1-(1,1-diMethylethyl) 3-ethyl ester, Monohydrochloride, (3S,4R)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Pyrrolidinedicarboxylic acid, 4-[[(1R)-1-phenylethyl]aMino]-, 1-(1,1-diMethylethyl) 3-ethyl ester, Monohydrochloride, (3S,4R)- (9CI)(346610-81-9)
• EPA Substance Registry System: 1,3-Pyrrolidinedicarboxylic acid, 4-[[(1R)-1-phenylethyl]aMino]-, 1-(1,1-diMethylethyl) 3-ethyl ester, Monohydrochloride, (3S,4R)- (9CI)(346610-81-9)

Safety Data

• Hazardous Substances Data: 346610-81-9(Hazardous Substances Data)

Usage

Chemical structure

The compound consists of a pyrrolidine ring, a carboxylic acid group, an amino group, an ethyl ester group, and a monohydrochloride component.

Chirality

It is a chiral molecule with a stereocenter at the 3rd and 4th positions.

Stereochemistry

The specific stereochemistry is (3S,4R), indicating the configuration of the chiral centers.

Derivative

It is a derivative of pyrrolidinedicarboxylic acid.

Applications

The compound is commonly used in biochemical research and pharmaceutical development due to its potential biological activity.

Structure-activity relationships

Its specific stereochemistry and substitution pattern make it an important molecule in the study of structure-activity relationships in drug design.

Nomenclature

The compound is named according to the IUPAC rules, with the prefix "1,3-Pyrrolidinedicarboxylic acid" indicating the presence of a pyrrolidine ring with two carboxylic acid groups at the 1st and 3rd positions, followed by the substituents and their positions.

Salt form

The compound is a monohydrochloride, indicating the presence of a single hydrogen chloride (HCl) molecule as a counterion.

Optical activity

As a chiral molecule, it may exhibit optical activity, which can be important for its biological activity and pharmacological effects.

Upstream product

• 2627-86-3 (S)-1-phenyl-ethylamine 
• 146256-98-6 4-oxo-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 14719-37-0 ethyl 2-(tert-butoxycarbonylamino)acetate 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 346610-79-5 (3R,4S)-1-(N-tert-butoxycarbonyl)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-hydroxycarbonylpyrrolidine 
• 369623-85-8 (3R,4S)-4-Amino-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 
• 895243-98-8 (3R,4S)-4-Amino-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl 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.

An efficient route to either enantiomer of orthogonally protected trans-3-Aminopyrrolidine-4-carboxylic acid

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