88815-87-6

Usage

Use

Building block for drug synthesis The compound is commonly used as a building block for the synthesis of various drugs and molecules.

Protection

t-Butoxycarbonyl (Boc) protected form The compound is a Boc protected form of 2-pyrrolidinecarboxylic acid, which makes it particularly useful for solid-phase peptide synthesis and other organic chemistry applications.

Physical form

White crystalline powder The compound appears as a white crystalline powder.

Molecular weight

250.33 g/mol This is the mass of one mole of the compound, expressed in grams.

Safety

Handle with care and follow proper protocols Due to its potential hazards and reactivity, it is important to handle and store this chemical with care and follow appropriate safety guidelines.

Upstream product

• 3392-10-7 tert-butoxycarbonyl-L-proline N-hydroxysuccinimide ester 
• 74-89-5 methylamine 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 593-51-1 methylamine hydrochloride 
• 147-85-3 L-proline 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 137693-34-6 DL-Pro-NHMe 
• 52060-82-9 L-proline methylamide 
• 59936-29-7 (S)-N-(tert-butoxycarbonyl)proline methyl ester 
• 1392268-79-9 (S)-1-(1-benzyl-1H-benzo[d]imidazol-2-yl)-N-((1-((1-benzyl-1H-benzo[d]imidazol-2-yl)methyl)pyrrolidin-2-yl)methyl)-N-methylmethanamine 
• 155540-08-2 acryloyl-L-prolyl-N'-methylamide 
• 19701-85-0 N-acetyl-L-proline-N'-methylamide 
• 33208-98-9 pyrrolidine-2-carboxylic acid methylamide hydrochloride 

Relevant academic research and scientific papers

Factors Affecting Conformation in Proline-Containing Peptides

(Equation presented) NMR was used to study the thermodynamics of the cis → trans isomerization for prolyl amide bonds in the compounds shown. The magnitude of Kt/c for C-terminal esters is greater than for the corresponding amides, signifying s

Double-chiral binaphthalene O-N-N tridentate ligand and preparation method thereof

The invention discloses a bis-chiral binaphthalene O-N-N tridentate ligand and a preparation method thereof. The ligand has the structural formula shown in formula (L). The preparation method comprises the following steps: (1) taking chiral 2 - methyl -2 - methoxy -binaphthalene as a raw material and replacing the reaction with an aromatic ring. As an alternative to the hydroxy protecting group, a brominated derivative (compound IV) is obtained by bromination. (2) Starting from protected chiral proline, a variety of diamine structures are obtained by conversion (Compound B). (3) Compound IV and Compound B are coupled in the presence of a catalyst in the presence of a catalyst to obtain a binaphthalene O-N-N tridentate ligand with bichirality. The ligand preparation method is simple in raw material, and has important significance for asymmetric organic synthesis.

A General Strategy to Enhance Donor-Acceptor Molecules Using Solvent-Excluding Substituents

While organic donor-acceptor (D-A) molecules are widely employed in multiple areas, the application of more D-A molecules could be limited because of an inherent polarity sensitivity that inhibits photochemical processes. Presented here is a facile chemical modification to attenuate solvent-dependent mechanisms of excited-state quenching through addition of a β-carbonyl-based polar substituent. The results reveal a mechanism wherein the β-carbonyl substituent creates a structural buffer between the donor and the surrounding solvent. Through computational and experimental analyses, it is demonstrated that the β-carbonyl simultaneously attenuates two distinct solvent-dependent quenching mechanisms. Using the β-carbonyl substituent, improvements in the photophysical properties of commonly used D-A fluorophores and their enhanced performance in biological imaging are shown.

Solution structural features of N-acyl homoserine lactones

Here we demonstrate that in interbacterial quorum signal moderators, N-acylhomoserine lactones (AHLs), the stabilization of bioactive pharmacophore lactone against lysis is through the e- withdrawing N-acyl motif which reduces lactone carbonyl polarization. This lysis is assisted by weak (-1) contacts between N-acyl O and lactone C′. The interactions that preclude this weak contact, in the free and receptor-bound AHLs, improve lactone halflife and hence are key to the design of the antibacterial AHL analogues.

Manganese catalysts with C1-symmetric N4 ligand for enantioselective epoxidation of olefins

Bioinspired manganese complexes based on N4 ligands, with a more rigid, chiral diamine derived from proline and two benzimidazoles, were synthesized and applied to epoxidize olefins with hydrogen peroxide as a clean oxidant. Notably, 60-99 % isolated yields and excellent ee values (up to 95 %) were obtained by using low catalyst loadings (0.01-0.2 mol %; see scheme; F green, S yellow). Copyright

Compounds binding to the S2-S3 pockets of thrombin

A set of compounds designed to bind to the S2-S3 pockets of thrombin was prepared. These compounds included examples with no interactions in the S1 pocket. Proline, a common P2 in many thrombin inhibitors, was combined with known P3 residues and P1 substituents of varying size and lipophilicity. Binding constants were determined using surface plasmon resonance (SPR) biosensor technology and were found to be in good agreement with results from an enzyme assay. A dramatic increase in affinity (100-1000 times) was seen for compounds incorporating an amino group capable of forming a hydrogen bond with gly216 in the protein backbone. The ligand efficiency was increased by including substituents that form stronger hydrophobic interactions with the P1 pocket. The binding mode was confirmed by X-ray analysis, which revealed the anticipated binding motif that included hydrogen bonds as well as a tightly bound water molecule. A QSAR model indicated that hydrogen bonding and lipophilicity were important for the prediction of binding constants. The results described here may have implications for how directed compound libraries for shallow protein pockets, like S2 and S3 in serine proteases, can be designed.

Highly efficient stereoconservative amidation and deamidation of α-amino acids

(Chemical Equation Presented) An overall stereoconservative protection and deprotection method of amino and carboxyl groups is presented. N-Phthaloyl N-alkyl secondary amides of α-amino acids can be generated from corresponding N-phthaloyl amino acids by coupling reaction of N-alkylamines using mixed anhydride method. These secondary amides can be transformed by thermal rearrangement of intermediate nitrosoamides to O-alkyl esters with retention of configuration and excellent yields.

First successful synthesis of acryloyl-L-prolylamide derivatives

Acryloyl-L-prolylamide (1b) and its two simple derivatives, acryloyl-L- propyl-N',N'-dimethylamide (1a) and acryloyl-L-prolyl-N'-methylamide (1c), were synthesized for the first time.