Category: 2418-95-3

Darguzyte, Milita published the artcileInfluence of Riboflavin Targeting on Tumor Accumulation and Internalization of Peptostar Based Drug Delivery Systems, Product Details of C11H22N2O4, the publication is Bioconjugate Chemistry (2020), 31(12), 2691-2696, database is CAplus and MEDLINE.

Riboflavin carrier protein (RCP) and riboflavin transporters (RFVTs) have been reported to be highly overexpressed in various cancer cells. Hence, targeting RCP and RFVTs using riboflavin may enhance tumor accumulation and internalization of drug delivery systems. To test this hypothesis, butyl-based 3-arm peptostar polymers were synthesized consisting of a lysine core (10 units per arm) and a sarcosine shell (100 units per arm). The end groups of the arms and the core were successfully modified with riboflavin and the Cy5.5 fluorescent dye, resp. While in phosphate buffered saline the functionalized peptostars showed a bimodal behavior and formed supramol. structures over time, they were stable in the serum maintaining their hydrodynamic diameter of 12 nm. Moreover, the polymers were biocompatible and the uptake of riboflavin targeted peptostars in A431 and PC3 cells was higher than in nontargeted controls and could be blocked competitively. In vivo, the polymers showed a moderate passive tumor accumulation, which was not significantly different between targeted and nontargeted peptostars. Nonetheless, at the histol. level, internalization into tumor cells was strongly enhanced for the riboflavin-targeted peptostars. Based on these results, we conclude that passive accumulation is dominating the accumulation of peptostars, while tumor cell internalization is strongly promoted by riboflavin targeting.

Bioconjugate Chemistry published new progress about 2418-95-3. 2418-95-3 belongs to amides-buliding-blocks, auxiliary class Chiral,Carboxylic acid,Amine,Aliphatic hydrocarbon chain,Ester,Amino acide derivatives, name is H-Lys(Boc)-OH, and the molecular formula is C11H22N2O4, Product Details of C11H22N2O4.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Karatzas, Anastasis published the artcileMacromolecular Architecture and Encapsulation of the Anticancer Drug Everolimus Control the Self-Assembly of Amphiphilic Polypeptide-Containing Hybrids, Application of H-Lys(Boc)-OH, the publication is Biomacromolecules (2019), 20(12), 4546-4562, database is CAplus and MEDLINE.

Macromol. architecture plays an important role in the self-assembly process of block copolymer amphiphiles. Herein, two series of stimuli-responsive amphiphilic 3-miktoarm star hybrid terpolypeptides and their corresponding linear analogs were synthesized exhibiting the same overall composition and mol. weight but different macromol. architecture. The macromol. architecture was found to be a key parameter in defining the morphol. of the nanostructures formed in aqueous solutions as well as to alter the self-assembly behavior of the polymers independently of their composition In addition, it was found that the assemblies prepared from the star-shaped polymers showed superior tolerance against enzymic degradation due to the increased corona block d. on the outer surface of the nanoparticles. Encapsulation of the hydrophobic anticancer drug Everolimus resulted in the formation of intriguing non-spherical and non-sym. pH-responsive nanostructures, such as “stomatocytes” and “multi-compartmentalized suprapolymersomes”, while the pH-triggered release of the drug was also investigated. Owing to the similarities of the developed “stomatocytes” with red blood cells, in combination with their pH-responsiveness and superior stability over enzymic degradation, they are expected to present advanced drug delivery properties and have the ability to bypass several extra- and intracellular barriers to reach and effectively treat cancer cells.

Biomacromolecules published new progress about 2418-95-3. 2418-95-3 belongs to amides-buliding-blocks, auxiliary class Chiral,Carboxylic acid,Amine,Aliphatic hydrocarbon chain,Ester,Amino acide derivatives, name is H-Lys(Boc)-OH, and the molecular formula is C11H22N2O4, Application of H-Lys(Boc)-OH.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Kabes, Connor Q. published the artcileSyntheses of enantiopure 1,2-ethylenediamines with tethered secondary amines of the formula H₂NCH₂CH[(CH₂)_nNHMe]NH₂ (n = 1 – 4) from α-amino acids: New agents for asymmetric catalysis, Category: amides-buliding-blocks, the publication is Synthesis (2020), 52(21), 3277-3285, database is CAplus.

Tris(hydrochloride) adducts of the title compounds are prepared from the inexpensive α-amino acids H₂N(C:O)CH₂CH(NH₂)CO₂H, HO(C:O)(CH₂)_nCH(NH ₂)CO ₂H (n = 1, 2), and H₂N(CH₂)₄CH(NH₂)CO₂H, resp. (steps/overall yield = 5/32%, 7/30%, 7/33%, 5/38%). The NH₂ group that is remote from the secondary amine is installed via BH₃ reduction of an amide [(C=O)NR₂] derived from an α-amino carboxylic acid. The MeNHCH₂ units are introduced by BH₃ reductions of alkyl carbamate [RO(C:O)NHCH₂; R = Et, t-Bu] or amide [MeHN(C:O)] moieties.

Synthesis published new progress about 2418-95-3. 2418-95-3 belongs to amides-buliding-blocks, auxiliary class Chiral,Carboxylic acid,Amine,Aliphatic hydrocarbon chain,Ester,Amino acide derivatives, name is H-Lys(Boc)-OH, and the molecular formula is C11H22N2O4, Category: amides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Wei, BinQing published the artcileDiscovery of Peptidomimetic Antibody-Drug Conjugate Linkers with Enhanced Protease Specificity, Quality Control of 2418-95-3, the publication is Journal of Medicinal Chemistry (2018), 61(3), 989-1000, database is CAplus and MEDLINE.

Antibody-drug conjugates (ADCs) have become an important therapeutic modality for oncol., with three approved by the FDA and over 60 others in clin. trials. Despite the progress, improvements in ADC therapeutic index are desired. Peptide-based ADC linkers that are cleaved by lysosomal proteases have shown sufficient stability in serum and effective payload-release in targeted cells. If the linker can be preferentially hydrolyzed by tumor-specific proteases, safety margin may improve. However, the use of peptide-based linkers limits our ability to modulate protease specificity. Here we report the structure-guided discovery of novel, nonpeptidic ADC linkers. We show that a cyclobutane-1,1-dicarboxamide-containing linker is hydrolyzed predominantly by cathepsin B while the valine-citrulline dipeptide linker is not. ADCs bearing the nonpeptidic linker are as efficacious and stable in vivo as those with the dipeptide linker. Our results strongly support the application of the peptidomimetic linker and present new opportunities for improving the selectivity of ADCs.

Journal of Medicinal Chemistry published new progress about 2418-95-3. 2418-95-3 belongs to amides-buliding-blocks, auxiliary class Chiral,Carboxylic acid,Amine,Aliphatic hydrocarbon chain,Ester,Amino acide derivatives, name is H-Lys(Boc)-OH, and the molecular formula is C7H8BNO4, Quality Control of 2418-95-3.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Tomlin, Frederick M. published the artcileSite-specific incorporation of quadricyclane into a protein and photocleavage of the quadricyclane ligation adduct, COA of Formula: C11H22N2O4, the publication is Bioorganic & Medicinal Chemistry (2018), 26(19), 5280-5290, database is CAplus and MEDLINE.

The quadricyclane (QC) ligation is a bioorthogonal reaction between a quadricyclane moiety and a nickel bis(dithiolene) derivative Here we show that a QC amino acid can be incorporated into a protein site-specifically using the pyrrolysine-based genetic code expansion platform, and subsequently used for ligation chem. Addnl., we exploited the photolability of the QC ligation product to render the adduct cleavable with a handheld UV lamp. We further developed a protein purification method that involves QC ligation of biotin to a protein of interest, capture on streptavidin resin, and finally release using only UV light. The QC ligation thus brings novel chem. manipulations to the realm of bioorthogonal chem.

Bioorganic & Medicinal Chemistry published new progress about 2418-95-3. 2418-95-3 belongs to amides-buliding-blocks, auxiliary class Chiral,Carboxylic acid,Amine,Aliphatic hydrocarbon chain,Ester,Amino acide derivatives, name is H-Lys(Boc)-OH, and the molecular formula is C8H12BNO5S, COA of Formula: C11H22N2O4.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Schneider, Nils published the artcileGenetic Code Expansion Method for Temporal Labeling of Endogenously Expressed Proteins, Quality Control of 2418-95-3, the publication is ACS Chemical Biology (2018), 13(11), 3049-3053, database is CAplus and MEDLINE.

The authors here present a method that combines genetic code expansion with CRISPR/Cas9 genome engineering to label endogenously expressed proteins with high spatiotemporal resolution The method exploits the use of an orthogonal tRNA/tRNA synthetase pair in conjugation with noncanonical amino acids to create stop codon read through events. To demonstrate the functionality of the method, the authors pulse labeled endogenous β-actin and tumor protein p53 with a minimally invasive HA tag at their C-termini. Targeting the protein label with a proximity ligation assay plus real time imaging facilitates seamless quantification of the protein synthesis rate and spatial localization at the single cell level. The presented approach does not interfere with any physiol. control of cellular expression, nor did any perturbation of endogenous protein functions. were observed

ACS Chemical Biology published new progress about 2418-95-3. 2418-95-3 belongs to amides-buliding-blocks, auxiliary class Chiral,Carboxylic acid,Amine,Aliphatic hydrocarbon chain,Ester,Amino acide derivatives, name is H-Lys(Boc)-OH, and the molecular formula is C11H22N2O4, Quality Control of 2418-95-3.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Bruyat, Pierrick published the artcileUse of an air-stable Cu(I)-NHC catalyst for the synthesis of peptidotriazoles, Category: amides-buliding-blocks, the publication is Journal of Organic Chemistry (2018), 83(21), 13515-13522, database is CAplus and MEDLINE.

We report the use of air-stable Cu(I)-NHC complex 4a as a catalyst for the efficient microwave-assisted synthesis of peptidotriazoles on solid phase. Compared with the usual conditions (CuI or CuSO₄/NaAsc), catalyst (I) allowed the preparation of a series of peptidomimetic compounds containing a 1,2,3-triazole ring in their backbone without the oxidation of common side-chains. Overall, the peptidotriazoles were obtained in good yields (61-87%), in excellent purity (higher than 94%) and with low copper contamination.

Journal of Organic Chemistry published new progress about 2418-95-3. 2418-95-3 belongs to amides-buliding-blocks, auxiliary class Chiral,Carboxylic acid,Amine,Aliphatic hydrocarbon chain,Ester,Amino acide derivatives, name is H-Lys(Boc)-OH, and the molecular formula is C11H22N2O4, Category: amides-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Mideksa, Yonatan G. published the artcileSite-Specific Protein Labeling with Fluorophores as a Tool To Monitor Protein Turnover, Product Details of C11H22N2O4, the publication is ChemBioChem (2020), 21(13), 1861-1867, database is CAplus and MEDLINE.

Proteins that terminally fail to acquire their native structure are detected and degraded by cellular quality control systems. Insights into cellular protein quality control are key to a better understanding of how cells establish and maintain the integrity of their proteome and of how failures in these processes cause human disease. Here we have used genetic code expansion and fast bio-orthogonal reactions to monitor protein turnover in mammalian cells through a fluorescence-based assay. We have used immune signaling mols. (interleukins) as model substrates and shown that our approach preserves normal cellular quality control, assembly processes, and protein functionality and works for different proteins and fluorophores. We have further extended our approach to a pulse-chase type of assay that can provide kinetic insights into cellular protein behavior. Taken together, this study establishes a minimally invasive method to investigate protein turnover in cells as a key determinant of cellular homeostasis.

ChemBioChem published new progress about 2418-95-3. 2418-95-3 belongs to amides-buliding-blocks, auxiliary class Chiral,Carboxylic acid,Amine,Aliphatic hydrocarbon chain,Ester,Amino acide derivatives, name is H-Lys(Boc)-OH, and the molecular formula is C11H22N2O4, Product Details of C11H22N2O4.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Robertson, Wesley E. published the artcileSense codon reassignment enables viral resistance and encoded polymer synthesis, Formula: C11H22N2O4, the publication is Science (Washington, DC, United States) (2021), 372(6546), 1057-1062, database is CAplus and MEDLINE.

It is widely hypothesized that removing cellular tRNAs (tRNAs)-making their cognate codons unreadable-might create a genetic firewall to viral infection and enable sense codon reassignment. However, it has been impossible to test these hypotheses. In this work, following synonymous codon compression and laboratory evolution in Escherichia coli, we deleted the tRNAs and release factor 1, which normally decode two sense codons and a stop codon; the resulting cells could not read the canonical genetic code and were completely resistant to a cocktail of viruses. We reassigned these codons to enable the efficient synthesis of proteins containing three distinct noncanonical amino acids. Notably, we demonstrate the facile reprogramming of our cells for the encoded translation of diverse noncanonical heteropolymers and macrocycles.

Science (Washington, DC, United States) published new progress about 2418-95-3. 2418-95-3 belongs to amides-buliding-blocks, auxiliary class Chiral,Carboxylic acid,Amine,Aliphatic hydrocarbon chain,Ester,Amino acide derivatives, name is H-Lys(Boc)-OH, and the molecular formula is C11H22N2O4, Formula: C11H22N2O4.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics

Isley, Nicholas A. published the artcileTotal Synthesis and Stereochemical Assignment of Streptide, Recommanded Product: H-Lys(Boc)-OH, the publication is Journal of the American Chemical Society (2019), 141(43), 17361-17369, database is CAplus and MEDLINE.

Streptide is a peptide-derived macrocyclic natural product that has attracted considerable attention since its discovery in 2015. It contains an unprecedented post-translational modification that intramolecularly links the β-carbon (C3) of a residue 2 lysine with the C7 of a residue 6 tryptophan, thereby forming a 20-membered cyclic peptide. Herein, we report the first total synthesis of streptide that confirms the regiochem. of the lysine-tryptophan crosslink and provides an unambiguous assignment of the stereochem. (3R vs 3S) of the lysine-2 C3 center. Both the 3R and the originally assigned 3S lysine diastereomers were independently prepared by total synthesis and it is the former, not the latter, that was found to correlate with the natural product. The approach enlists a powerful Pd(0)-mediated indole annulation for the key macrocyclization of the complex core peptide, utilizes an underdeveloped class of hypervalent iodine(III) aryl substrates in a palladium-catalyzed C-H activation/β-arylation reaction conducted on a lysine derivative, and provides access to material with which the role of streptide and related natural products may be examined

Journal of the American Chemical Society published new progress about 2418-95-3. 2418-95-3 belongs to amides-buliding-blocks, auxiliary class Chiral,Carboxylic acid,Amine,Aliphatic hydrocarbon chain,Ester,Amino acide derivatives, name is H-Lys(Boc)-OH, and the molecular formula is C11H22N2O4, Recommanded Product: H-Lys(Boc)-OH.

Referemce:
https://en.wikipedia.org/wiki/Amide,
Amide – an overview | ScienceDirect Topics