41863-49-4

Upstream product

• 4530-20-5 BOC-glycine 
• 2133-40-6 L-proline methyl ester monohydrochloride 
• 2577-48-2 methyl (2S)-pyrrolidine carboxylate 
• 67084-40-6 1-(N-tert-butoxycarbonyl-glycyloxy)-1H-benzotriazole 
• 147-85-3 L-proline 
• 24424-99-5 di-tert-butyl dicarbonate 
• 14296-92-5 (S)-1-(2-(tert-butoxycarbonylamino)acetyl)pyrrolidine-2-carboxylic acid 
• 74-88-4 methyl iodide 

Downstream Products

• 14296-92-5 (S)-1-(2-(tert-butoxycarbonylamino)acetyl)pyrrolidine-2-carboxylic acid 
• 849094-31-1 Boc-Pro-Phe-Ser-Phe-Gly-Pro-Leu-Ala-OMe 
• 849094-32-2 Boc-Pro-Phe-Ser-Phe-Gly-Pro-Leu-Ala-O-C₆H₄-NO₂-p 
• 361541-79-9 Boc-Gly-Pro-Pro-Phe-OMe 
• 361541-80-2 Boc-Gly-Ile-Gly-Gly-Gly-Pro-Pro-Phe-OMe 
• 3705-27-9 (S)-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 
• 1186293-72-0 Boc-Gly-Pro-Arg-AMC*HCl 
• 47295-77-2 Gly-Pro-Arg 
• 1374558-53-8 N,N-dibenzyl-glycinyl-L-proline methyl ester 
• 704-15-4 H-Gly-Pro-OH 

Relevant academic research and scientific papers

Gold(i) thiolates containing amino acid moieties. Cytotoxicity and structure-activity relationship studies

Several gold(i) complexes containing a thiolate ligand functionalised with several amino acid or peptide moieties of the type [Au(SPyCOR)(PPh2R′)] (where R = OH, amino acid or dipeptide and R′ = Ph or Py) were prepared. These thiolate gold comp

Synthesis and evaluation of hybrid molecules targeting the vinca domain of tubulin

Some hybrids of vinca alkaloids and phomopsin A, linked by a glycine pattern, have been synthesized in one or two steps, by an insertion reaction and shown to inhibit microtubule assembly. These compounds have been elaborated in order to interact with both the "vinca site" and the "peptide site" of the vinca domain in tubulin. Two out of three hybrids are potent inhibitors of microtubules assembly and they present good cytotoxicity against different cell lines. Molecular modelling studies show that they could bind, within the vinca domain, in similar spatial regions as those of vinca and phomopsin thanks to the flexibility provided by the glycine linker used to elaborate these hybrids. This journal is

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.

Two-Dimensional Barriers for Probing Conformational Shifts in Macrocycles

We describe the development and use of composite two-dimensional barriers in macrocyclic backbones. These tunable constructs derive their mode of action from heterocyclic rearrangements. The Boulton-Katritzky reaction has been identified as a particularly versatile means to effect a composite barrier, allowing the examination of the influence of heterocycle translocation on conformation. Kinetic studies using 1H NMR have revealed that the in-plane atom movement is fast in 17, 18, 19-membered rings but slows down in 16-membered rings. The analysis by NMR and MD simulation experiments is consistent with the maintenance of rare cis-amide motifs during conformational interconversion. Taken together, our investigation demonstrates that heterocyclic rearrangement reactions can be used to control macrocyclic backbones and provides fundamental insights that may be applicable to the development of a wide range of other conformational control elements.

STAT DEGRADERS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same.

Phenysilane and Silicon Tetraacetate: Versatile Promotors for Amide Synthesis

Phenylsilane was reevaluated as a useful coupling reagent for amide synthesis. At room temperature, a wide range of amides and peptides were obtained in good to excellent yields (up to 99 %). For the first time, Weinreb amides synthesis mediated by a hydrosilane were also documented. Comparative experiments with various acetoxysilanes suggested the involvement of a phenyl-triacyloxysilane. From this mechanistic study, silicon tetraacetate was shown as an efficient amine acylating agent.

The Study of Stability of Proline-Containing Derivatives of Dopamine and Serotonin in the Biological Media in Vitro Experiments

Abstract—: The peptides Boc-Gly-Pro-DP, Z-Gly-Pro-DP, LA-Gly-Pro-DP, Boc-Gly-Pro-Srt, Z-Gly-Pro-Srt have been synthesized for the first time. The study of their stability in the presence of leucine aminopeptidase, carboxypeptidase Y, carboxypeptidase B, and proline endopeptidase (PEP) has shown that the synthesized peptides are stable in the presence of aminopeptidases and carboxypeptidases. In the presence of PEP, dopamine (DP) and serotonin (Srt) have been cleaved from these substances. Thus, the originally synthesized proline derivatives of Srt and DP may be considered as the resources, from which Srt and DP can be gradually released. This creates the possibility of a prolonged action of these biologically active compounds on cells and, consequently, on the whole body.

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.

Iridium-Catalyzed Reductive Strecker Reaction for Late-Stage Amide and Lactam Cyanation

A new iridium-catalyzed reductive Strecker reaction for the direct and efficient formation of α-amino nitrile products from a broad range of (hetero)aromatic and aliphatic tertiary amides, and N-alkyl lactams is reported. The protocol exploits the mild and highly chemoselective reduction of the amide and lactam functionalities using IrCl(CO)[P(C6H5)3]2 (Vaska's complex) in the presence of tetramethyldisiloxane, as a reductant, to directly generate hemiaminal species able to undergo substitution by cyanide upon treatment with TMSCN (TMS=trimethylsilyl). The protocol is simple to perform, broad in scope, efficient (up to 99 % yield), and has been successfully applied to the late-stage functionalization of amide- and lactam-containing drugs, and naturally occurring alkaloids, as well as for the selective cyanation of the carbonyl carbon atom linked to the N atom of proline residues within di- and tripeptides.

Synthesis, characterization and biological screening of diandrine A

Synthesis of a proline-rich cyclic hexapeptide - diandrine A [VI] was accomplished by coupling of tetrapeptide unit Boc-Gly-Pro-Trp-Pro-OH with dipeptide unit Tyr-Phe-OMe followed by cyclization of linear peptide unit [V] under alkaline condition. Structu