92132-25-7

Upstream product

• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 616-34-2 methoxycarbonylmethylamine 
• 5680-79-5 glycine ethyl ester hydrochloride 
• 15761-39-4 N-tert-butoxycarbonyl-proline 
• 84890-94-8 (S)-2-Isobutoxycarbonyloxycarbonyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 37784-17-1 N-(tert-butoxycarbonyl)-D-proline 
• 24424-99-5 di-tert-butyl dicarbonate 
• 344-25-2 D-Prolin 
• 51785-82-1 N-tert-butyloxycarbonyl-L-prolylglycine 
• 74-88-4 methyl iodide 
• 147-85-3 L-proline 
• 24608-52-4 tert-butyl chloroformate 
• 133010-05-6 tert-butyl 2-(fluorocarbonyl)pyrrolidine-1-carboxylate 

Downstream Products

• 100008-17-1 N^α-Boc-L-phenylalanyl-L-prolyl-glycine methyl ester 
• 31953-80-7 N-tert-butyloxycarbonyl-(2S)-prolyl-glycine benzyl ester 
• 634922-10-4 [(pyrrolidine-2-carbonyl)-amino]acetic acid methyl ester trifluoroacetate 
• 1370659-19-0 C₂₈H₄₁N₅O₉ 
• 1370659-20-3 C₂HF₃O₂*C₂₃H₃₃N₅O₇ 
• 634922-10-4 (R)-(+)-prolylglycine methyl ester trifluoroacetate 
• 250290-80-3 Boc-^DPro-Gly-OH 
• 3705-27-9 (S)-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 
• 1423168-04-0 cyclo-D-Pro-L-(Phe-Pro-His-Pro-Pro-Gly-Leu) 
• 134053-86-4 (3S,6S)-3-methoxy-1,6-trimethylene-2,5-piperazinedione 
• 100101-21-1 Boc-Tyr-Pro-Phe-Pro-Gly-OMe 
• 2578-57-6 N-prolylglycine 
• 85651-86-1 N-tert-butyloxycarbonyl-O-benzyl-L-tyrosyl-L-prolyl-L-phenylalanyl-L-prolylglycyl-L-prolyl-L-isoleucine 

Relevant academic research and scientific papers

Bioinspired modular synthesis of elastin-mimic polymers to probe the mechanism of elastin elasticity

Bioinspired modular synthesis of elastin-mimic polymers (EMPs) is achieved via Cu-catalyzed alkyne-azide cyclization (CuAAC). By changing the module, EMPs with different secondary structures determined by circular dichroism (CD) spectra in trifluoroethanol (TFE) solution are obtained. The EMPs are characterized by measuring the lower critical solution temperatures (LSCTs) and the bulk mechanic properties under the conditions of both dry and hydrated forms. The unique molecular design enables us to probe mechanistic questions and assess the structure-property relationship of the EMPs. Our results indicate that, instead of a highly organized secondary structure, hydrophobic hydration is critical for the elasticity of EMPs.

N-Terminal Selective C?H Azidation of Proline-Containing Peptides: a Platform for Late-Stage Diversification

A methodology for the C?H azidation of N-terminal proline-containing peptides was developed employing only commercially available reagents. Peptides bearing a broad range of functionalities and containing up to 6 amino acids were selectively azidated at the carbamate-protected N-terminal residue in presence of the numerous other functional groups present on the molecules. Post-functionalizations of the obtained aminal compounds were achieved: cycloaddition reactions or C?C bond formations via a sequence of imine formation/nucleophilic addition were performed, offering an easy access to diversified peptides.

Highly Diastereoselective Synthesis of Cyclic α-Aminophosphonic and α-Aminophosphinic Acids from Glycyl-l-Proline 2,5-Diketopiperazine

This paper describes the first diastereoselective synthesis of cyclic α-aminophosphonic and α-amino phosphonic acids from glycyl-l-proline 2,5-diketopiperazine (S)-6 prepared according to the usual peptide coupling procedures. The highlights of this contribution is the chemoselective reduction of the carbamate-imide activated carbonyl group in the N-Boc 2,5-diketopiperazine (S)-11 to generate the unstable hemiaminals (1R,8aS)-12 and (1S,8aS)-13, followed by the highly diastereoselective nucleophilic addition of trimethyl phosphite or dimethyl phenylphosphonite to the chiral carbenium ion (S)-5. Acid hydrolysis of the phosphonate and phosphinate functionalities with simultaneous cleavage of the tert-butyl carbamate protecting group led to the target compounds. The high diastereoselectivity in the nucleophilic addition of trivalent phosphorus to the chiral carbenium ion (S)-5 is in agreement with our precedent reports.

A bio-inspired approach to proline-derived 2,4-disubstituted oxazoles

A convenient four-step approach to the synthesis of (S)-4-alkyl-2-(pyrrolidin-2-yl)oxazoles starting from l-Boc-proline inspired by naturally occurring oxazole-containing peptidomimetics is described. The key step is the cyclization of 1-Boc-N-(1-oxoalkan

Total Synthesis of the Cyclic Dodecapeptides Wewakazole and Wewakazole B

The cyclic dodecapeptides wewakazole and wewakazole B have been synthesized by a divergent strategy via a common tris-proline containing oxazole octapeptide and two separate bis-oxazole containing tetrapeptide units, followed by peptide coupling and macro

Aggregation propensity of amyloidogenic and elastomeric dipeptides constituents

This study demonstrates the self-assembly of N- and C-terminal protected dipeptides Phe–Gly and Pro–Gly which were derived from amyloidogenic and elastomeric peptide sequences. These constituents afforded nanostructured supramolecular ensembles through va

9-Silafluorenyl Dichlorides as Chemically Ligating Coupling Agents and Their Application in Peptide Synthesis

A fundamentally simple, mild, and practical procedure for peptide bond formation is reported that employs a stoichiometric amount of easy-to-access 9-silafluorenyl dichlorides as the coupling agent. Without initial preactivation or elaboration of the carboxylic acid or amine termini of the amino acids, the developed reagent is proposed to act through an unprecedented chemical ligation mechanism, bringing the two coupling partners together before being subsequently eliminated. The desired amides or peptide bonds are thus furnished in good yields and with low to no epimerization.

Distal Stereocontrol Using Guanidinylated Peptides as Multifunctional Ligands: Desymmetrization of Diarylmethanes via Ullman Cross-Coupling

We report the development of a new class of guanidine-containing peptides as multifunctional ligands for transition-metal catalysis and its application in the remote desymmetrization of diarylmethanes via copper-catalyzed Ullman cross-coupling. Through design of these peptides, high levels of enantioinduction and good isolated yields were achieved in the long-range asymmetric cross-coupling (up to 93:7 er and 76% yield) between aryl bromides and malonates. Our mechanistic studies suggest that distal stereocontrol is achieved through a Cs-bridged interaction between the Lewis-basic C-terminal carboxylate of the peptides with the distal arene of the substrate.

A general method for the facile synthesis of optically active 2-substituted piperazines via functionalized 2,5-diketopiperazines

Upon utilization of some common methods described in the literature for the synthesis of chiral, 2-substituted 2,5-diketopiperazines, extensive racemization was observed. Further investigation showed that heating in the presence of a mild base racemized the chiral center in the product diketopiperazines. A generalized, readily scalable route was sought and, after investigating the effect of base and temperature, conditions were identified that promoted cyclization without erosion of enantiomeric excess. An array of functionalization was tolerated and this procedure serves as a useful and reliable method for the facile synthesis of this important class of compounds.

Nucleophilic ring-opening of benzoxazinones by DBU: Some observations

This communication demonstrates the formation of an unusual nucleophilic ring opening of benzoxazinones by 1,8-diazabicycloundec-7-ene (DBU). This observation contradicts the intrinsic feature of a hindered nonnucleophilic base like DBU. Confirmation of t