Category: 71989-31-6

Chavda, Jaydeepsinh published the artcileBODIPY-peptide conjugate: Synthesis, photo-physical and cell viability studies, Product Details of C20H19NO4, the publication is Journal of Porphyrins and Phthalocyanines (2021), 25(10/12), 1230-1239, database is CAplus.

The synthesis and biol. studies of BODIPY-GPR peptide conjugate (BD-2) are reported. As compared to the parent BODIPY (BD-1), the peptide linked BD-2showed blue shifted absorption and emission with excellent Stokes shift of 201 nm. Mol. docking studies on EGFR protein kinase indicated very efficient binding affinity of BD-2 as compared to the standard drug (Erlotinib). The cell viability experiments of BD-2on normal (HEK293T) and lung cancer (A549) cell lines indicated 85-95% viability. Bioimaging studies showed that, BD-2was able to penetrate the lung cancer cell line.

Journal of Porphyrins and Phthalocyanines published new progress about 71989-31-6. 71989-31-6 belongs to catalysis-chemistry, auxiliary class Amino acide derivatives,pyrrolidine, name is Fmoc-Pro-OH, and the molecular formula is C20H19NO4, Product Details of C20H19NO4.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Lopez, John published the artcileMissing link: enabling loading of 2-chlorotrityl chloride resin in N-butylpyrrolidinone as a green solvent, Recommanded Product: Fmoc-Pro-OH, the publication is Organic Process Research & Development (2022), 26(5), 1450-1457, database is CAplus.

The 2-chlorotrityl chloride (2-CTC) resin is one of the most frequently used and most versatile resins for the large-scale manufacture of peptides. As a part of our efforts in greening solid-phase peptide synthesis, here, we disclose an efficient procedure for the loading of the first amino acid onto the 2-CTC resin using the green solvent N-butylpyrrolidinone. By applying a design of experiment models, key critical process parameters such as amino acid equivalent and water content were identified. The results obtained suggest that the conditions found can be generalized and applied to any Fmoc-amino acid (Fmoc = 9-fluorenylmethoxycarbonyl). Moreover, they serve as a starting point for the optimization of green resin loading.

Organic Process Research & Development published new progress about 71989-31-6. 71989-31-6 belongs to catalysis-chemistry, auxiliary class Amino acide derivatives,pyrrolidine, name is Fmoc-Pro-OH, and the molecular formula is C20H19NO4, Recommanded Product: Fmoc-Pro-OH.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Berger, Or published the artcileMussel Adhesive-Inspired Proteomimetic Polymer, Name: Fmoc-Pro-OH, the publication is Journal of the American Chemical Society (2022), 144(10), 4383-4392, database is CAplus and MEDLINE.

Herein, a synthetic polymer proteomimetic is described that reconstitutes the key structural elements and function of mussel adhesive protein. The proteomimetic was prepared via graft-through ring-opening metathesis polymerization of a norbornenyl-peptide monomer. The peptide was derived from the natural underwater glue produced by marine mussels that is composed of a highly repetitive 10 amino acid tandem repeat sequence. The hypothesis was that recapitulation of the repeating unit in this manner would provide a facile route to a nature-inspired adhesive. To this end, the material, in which the arrangement of peptide units was as side chains on a brush polymer rather than in a linear fashion as in the natural protein, was examined and compared to the native protein. Mech. measurements of adhesion forces between solid surfaces revealed improved adhesion properties over the natural protein, making this strategy attractive for diverse applications. One such application is demonstrated, using the polymers as a surface adhesive for the immobilization of live cells.

Journal of the American Chemical Society published new progress about 71989-31-6. 71989-31-6 belongs to catalysis-chemistry, auxiliary class Amino acide derivatives,pyrrolidine, name is Fmoc-Pro-OH, and the molecular formula is C20H19NO4, Name: Fmoc-Pro-OH.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

So, Wing Ho published the artcileOn-resin Ugi reaction for C-terminally modified and head-to-tail cyclized antibacterial peptides, Category: catalysis-chemistry, the publication is Organic Letters (2021), 23(21), 8277-8281, database is CAplus and MEDLINE.

Here we report a method to synthesize C-terminally modified peptides on resin. A four-component Ugi reaction of isocyanide resin, an Fmoc-protected (Fmoc = 9-fluorenylmethoxycarbonyl) amino acid, an amine, and a 6-nitroveratrylaldehyde gives C-terminal photo-caged peptide amides, which can be photolyzed to generate C-terminal peptide amides. Changing the amine component in the Ugi reaction gives peptides with different C-terminal modifications including substituted anilides, alkyne, and azide. By installing an N-terminal azide and C-terminal alkyne, we synthesized a head-to-tail cyclized antibacterial peptide through copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC). The cyclized peptide exhibited higher proteolytic stability and antibacterial activity than the linear peptide.

Organic Letters published new progress about 71989-31-6. 71989-31-6 belongs to catalysis-chemistry, auxiliary class Amino acide derivatives,pyrrolidine, name is Fmoc-Pro-OH, and the molecular formula is C26H45N5O7Si2, Category: catalysis-chemistry.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Laps, Shay published the artcileInsight on the order of regioselective ultrafast formation of disulfide bonds in (antimicrobial) peptides and miniproteins, Formula: C20H19NO4, the publication is Angewandte Chemie, International Edition (2021), 60(45), 24137-24143, database is CAplus and MEDLINE.

Disulfide-rich peptides and proteins are among the most fascinating bioactive mols. The difficulties associated with the preparation of these targets have prompted the development of various chem. strategies. Nevertheless, the production of these targets remains very challenging or elusive. Recently, we introduced a strategy for one-pot disulfide bond formation, tackling most of the previous limitations. However, the effect of the order of oxidation remained an underexplored issue. Herein we report on the complete synthetic flexibility of the approach with respect to the order of oxidation of three disulfide bonds in targets that lack the knot motif. In contrast, our study reveals an essential order of disulfide bond formation in the EETI-II knotted miniprotein. This synthetic strategy was applied for the synthesis of novel analogs of the plectasin antimicrobial peptide with enhanced activities against methicillin-resistant Staphylococcus aureus (MRSA), a notorious human pathogen.

Angewandte Chemie, International Edition published new progress about 71989-31-6. 71989-31-6 belongs to catalysis-chemistry, auxiliary class Amino acide derivatives,pyrrolidine, name is Fmoc-Pro-OH, and the molecular formula is C20H19NO4, Formula: C20H19NO4.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Chakraborty, Amit published the artcileChemoselective disulfide formation by thiol-disulfide interchange in SIT-protected cysteinyl peptides, Quality Control of 71989-31-6, the publication is Journal of Organic Chemistry (2022), 87(1), 708-712, database is CAplus and MEDLINE.

Chemoselective disulfide formation is accomplished through a thiol-disulfide interchange approach using sec-isoamyl mercaptan (SIT) as an alkyl sulfenyl-protecting group of one of the Cys residues involved in the pairing. SIT has a dual and unique characteristic, acting as a masking group during the synthesis and directing disulfide formation in the presence of a free thiol. This novel approach is illustrated by the synthesis of several peptides of biol. interest.

Journal of Organic Chemistry published new progress about 71989-31-6. 71989-31-6 belongs to catalysis-chemistry, auxiliary class Amino acide derivatives,pyrrolidine, name is Fmoc-Pro-OH, and the molecular formula is C20H19NO4, Quality Control of 71989-31-6.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Simov, Vladimir published the artcileDiscovery and characterization of novel peptide inhibitors of the NRF2/MAFG/DNA ternary complex for the treatment of cancer, Name: Fmoc-Pro-OH, the publication is European Journal of Medicinal Chemistry (2021), 113686, database is CAplus and MEDLINE.

Pathway activating mutations of the transcription factor NRF2 and its neg. regulator KEAP1 are strongly correlative with poor clin. outcome with pemetrexed/carbo(cis)platin/pembrolizumab (PCP) chemo-immunotherapy in lung cancer. Despite the strong genetic support and therapeutic potential for a NRF2 transcriptional inhibitor, currently there are no known direct inhibitors of the NRF2 protein or its complexes with MAF and/or DNA. Herein we describe the design of a novel and high-confidence homol. model to guide a medicinal chem. effort that resulted in the discovery of a series of peptides that demonstrate high affinity, selective binding to the Antioxidant Response Element (ARE) DNA and thereby displace NRF2-MAFG from its promoter, which is an inhibitory mechanism that to our knowledge has not been previously described. In addition to their activity in electrophoretic mobility shift (EMSA) and TR-FRET-based assays, we show significant dose-dependent ternary complex disruption of NRF2-MAFG binding to DNA by SPR, as well as cellular target engagement by thermal destabilization of HiBiT-tagged NRF2 in the NCI-H1944 NSCLC cell line upon digitonin permeabilization, and SAR studies leading to improved cellular stability. We report the characterization and unique profile of lead peptide (1), [(Ac-DELRAKALHIPFPVEKIINLPVVDFNEMMSKEQFN-EAQLALIRDIRRRGKNKVAAQNSRKRKLENIVELEQDLDHLKDEKEKGGhPraA-GSSG-K(DBCO-Cy5)-CONH₂)-(Ac-NGTSLTDEELVTMSVRELNQHLRGLSKEEIVQLKQRRRTLKNRGYAASSRVKRVTQKEELEKQKAELQQEVEKGGDabA-CONH₂)] which we believe to be a useful in vitro tool to probe NRF2 biol. in cancer cell lines and models, while also serving as an excellent starting point for addnl. in vivo optimization toward inhibition of NRF2-driven transcription to address a significant unmet medical need in non-small cell lung cancer (NSCLC).

European Journal of Medicinal Chemistry published new progress about 71989-31-6. 71989-31-6 belongs to catalysis-chemistry, auxiliary class Amino acide derivatives,pyrrolidine, name is Fmoc-Pro-OH, and the molecular formula is C26H41N5O7S, Name: Fmoc-Pro-OH.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Zhang, Fa published the artcileA viral insulin-like peptide is a natural competitive antagonist of the human IGF-1 receptor, Related Products of catalysis-chemistry, the publication is Molecular Metabolism (2021), 101316, database is CAplus and MEDLINE.

Natural sources of mol. diversity remain of utmost importance as a reservoir of proteins and peptides with unique biol. functions. We recently identified such a family of viral insulin-like peptides (VILPs). We sought to advance the chem. methods in synthesis to explore the structure-function relationship within these VILPs, and the mol. basis for differential biol. activities relative to human IGF-1 and insulin.Optimized chem. methods in synthesis were established for a set of VILPs and related analogs. These modified forms included the substitution of select VILP chains with those derived from human insulin and IGF-1. Each peptide was assessed in vitro for agonism and antagonism at the human insulin and the human insulin-like growth factor 1 receptor (IGF-1R).We report here that one of these VILPs, lymphocystis disease virus-1 (LCDV1)-VILP, has the unique property to be a potent and full antagonist of the IGF-1R. We demonstrate the coordinated importance of the B- and C-chains of the VILP in regulating this activity. Moreover, mutation of the glycine following the first cysteine in the B-chain of IGF-1 to serine, in concert with substitution to the connecting peptide of LCDV1-VILP, converted native IGF-1 to a high potency antagonist.The results reveal novel aspects in ligand-receptor interactions at the IGF-1 receptor and identify a set of antagonists of potential medicinal importance.

Molecular Metabolism published new progress about 71989-31-6. 71989-31-6 belongs to catalysis-chemistry, auxiliary class Amino acide derivatives,pyrrolidine, name is Fmoc-Pro-OH, and the molecular formula is C38H74Cl2N2O4, Related Products of catalysis-chemistry.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Naoum, Johnny N. published the artcileStirring peptide synthesis to a new level of efficiency, Category: catalysis-chemistry, the publication is Organic Process Research & Development (2022), 26(1), 129-136, database is CAplus.

Accelerating solid-phase synthesis is crucial for accessing a large number of peptides in a short time. Since standard peptide synthesis is usually done under poor diffusion conditions with slow or no mixing of the solid support, acceleration of the process is achieved by applying a large excess of reagents. In this work, overhead stirring and heating were combined to provide accelerated solid-phase peptide synthesis without using an excess of reagent. A new setup that allows both heating and fast stirring was designed specifically for research laboratory-scale peptide synthesis. By increasing the diffusion of both reagents and beads in a narrow dimension reactor, solid-phase reactions were done in seconds and medium-size peptides were synthesized in minutes.

Organic Process Research & Development published new progress about 71989-31-6. 71989-31-6 belongs to catalysis-chemistry, auxiliary class Amino acide derivatives,pyrrolidine, name is Fmoc-Pro-OH, and the molecular formula is C20H19NO4, Category: catalysis-chemistry.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Drayton, Matthew published the artcileEnzymatically releasable polyethylene glycol – host defense peptide conjugates with improved activity and biocompatibility, Formula: C20H19NO4, the publication is Journal of Controlled Release (2021), 220-231, database is CAplus and MEDLINE.

Host defense peptides (HDPs) have been the subject of great interest for the treatment of multidrug-resistant bacterial infections due to their multimodal activity and low induction of resistance. However, aggregation, toxicity, and short biol. half-life have limited their applicability for clin. treatment. Many methods have been explored to alleviate these issues, such as polymer (e.g., polyethylene glycol (PEG)) conjugation, but these are often accompanied by reductions in the activity of the HDP. Here, we detail the design of a novel PEG-HDP conjugate incorporating an enzymic cleavage sequence targeting matrix metalloproteinases (MMPs) that accumulate at sites of inflammation and infection. Addition of the cleavage sequence onto either the N- or the C-terminal region of the parent peptide (peptide 73, a derivative of the HDP aurein 2.2) was explored to determine the location for optimal antimicrobial activity following MMP cleavage; furthermore, the susceptibility of the peptide to MMP cleavage after conjugation to 2 kDa or 5 kDa PEG was examined The top candidate, L73, utilized an N-terminal cleavage site that was subsequently conjugated to a 2 kDa PEG polymer. Both L73 and the conjugate exhibited no antimicrobial activity in vitro until cleaved by purified MMP, which liberated a peptide fragment with 16- or 63-fold improved activity, resp., corresponding to a min. inhibitory concentration (MIC) of 8 μg/mL, comparable to that of peptide 73 (4 μg/mL). Furthermore, PEG conjugation improved the blood compatibility and reduced the aggregation tendency of the HDP in vitro, indicating enhanced biocompatibility. When administered as a single s.c. dose (âˆ?.6 mg, or a peptide concentration of 142 mg/kg) in a mouse abscess model of high-d. methicillin-resistant Staphylococcus aureus (MRSA) infection, the conjugate displayed strong activity, reducing abscess size and bacterial load by 73.3% and 58-fold, resp. This activity was completely lost when the cleavage site was rendered resistant to MMPs by the substitution of two D-amino acids, supporting the hypothesis that antimicrobial activity was dependent on cleavage by MMPs, which were shown here to increasingly accumulate at the abscess site up to 18 h post infection. Finally, the conjugate displayed biocompatibility in vivo, with no identifiable toxicity or aggregation.

Journal of Controlled Release published new progress about 71989-31-6. 71989-31-6 belongs to catalysis-chemistry, auxiliary class Amino acide derivatives,pyrrolidine, name is Fmoc-Pro-OH, and the molecular formula is C20H19NO4, Formula: C20H19NO4.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia