65559-51-5

Upstream product

• 1426327-18-5 C₆₈H₁₁₈N₂O₇ 
• 63-91-2 L-phenylalanine 
• 35661-40-6 N-Fmoc L-Phe 
• 1316293-48-7 methyl 2-(2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanamido)acetate 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 1161-13-3 N-Cbz-L-Phe 
• 3397-32-8 N-(benzyloxycarbonyl)-phenylalanine-N-hydroxysuccinimide ester 
• 51165-20-9 Z(OMe)-Phe-Gly-OMe 
• 7625-57-2 methyl 2-((2S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanamido)acetate 

Downstream Products

• 112372-40-4 Boc-Gln-Phe-Gly-OMe 
• 113807-28-6 N-Boc-D-alanyl-L-phenylalanyl-glycine methyl ester 
• 138891-24-4 Z(OMe)-D-Met-Phe-Gly-OMe 
• 65279-14-3 Benzyloxycarbonyl-L-leucyl-L-phenylalanyl-glycine methyl ester 
• 5037-75-2 cyclo(Gly-Phe) 
• 112372-41-5 Boc-Gln-Phe-Gly-NHNH₂ 
• 112372-49-3 H-Gln-Phe-Gly-Ser-Pro-Lys(Z)-OBzl 
• 112372-48-2 Boc-Gln-Phe-Gly-Ser-Pro-Lys(Z)-OBzl 
• 1098101-21-3 tert-butyloxycarbonyl-valyl-tyrosyl-phenylalanyl-glycine methyl ester 
• 1108208-41-8 (S)-methyl-2-(2-(cyanomethylamino)3-phenyl propanamido)acetate 
• 5037-75-2 cyclo-/glycyl-L-phenylalanyl/ 

Relevant academic research and scientific papers

Pd-Catalysed oxidative carbonylation of α-amino amides to hydantoins under mild conditions

The first example of palladium-catalysed oxidative carbonylation of unprotected α-amino amides to hydantoins is described here. The selective synthesis of the target compounds was achieved under mild conditions (1 atm of CO), without ligands and bases. The catalytic system overrode the common reaction pathway that usually leads instead to the formation of symmetrical ureas.

Synthesis, in vitro ADME profiling and in vivo pharmacological evaluation of novel glycogen phosphorylase inhibitors

A small set of indole-2-carboxamide derivatives identified from a high-throughput screening campaign has been described as a novel, potent, and glucose-sensitive inhibitors of glycogen phosphorylase a (GPa). Among this series of compounds, compound 2 exhibited moderate GP inhibitory activity (IC50 = 0.29 μM), good cellular efficacy (IC50 = 3.24 μM for HepG2 cells and IC50 = 7.15 μM for isolated rat hepatocytes), together with good absorption, distribution, metabolism, and elimination (ADME) profiles. The in vivo animal study revealed that compound 2 significantly inhibited an increase of fasting blood glucose level in adrenaline-induced diabetic mice.

Peptide-Chain Elongation Using Unprotected Amino Acids in a Micro-Flow Reactor

Conventional peptide synthesis requires a deprotection step after each amidation step, which decreases synthetic efficiency. Therefore, peptide synthesis using unprotected amino acids is considered an ideal approach. Here, we report peptide chain elongati

Engineered Substrate for Cyclooxygenase-2: A Pentapeptide Isoconformational to Arachidonic Acid for Managing Inflammation

Beyond the conventional mode of working of anti-inflammatory agents through enzyme inhibition, herein, COX-2 was provided with an alternate substrate. A proline-centered pentapeptide isoconformational to arachidonic acid, which exhibited appreciable selectivity for COX-2, overcoming acetic acid- and formalin-induced pain in rats to almost 80%, was treated as a substrate by the enzyme. Remarkably, COX-2 metabolized the pentapeptide into small fragments consisting mainly of di- and tripeptides that ensured the safe breakdown of the peptide under in vivo conditions. The kinetic parameter Kcat/Km for COX-2-mediated metabolism of the peptide (6.3 × 105 M-1 s-1) was quite similar to 9.5 × 105 M-1 s-1 for arachidonic acid. Evidenced by the molecular dynamic studies and the use of Y385F COX-2, it was observed that the breakage of the pentapeptide has probably been taken place through H-bond activation of the peptide bond by the side chains of Y385 and S530.

Synthesis and biological evaluation of novel FK228 analogues as potential isoform selective HDAC inhibitors

Novel C4- and C7-modified FK228 analogues were efficiently synthesized in a highly convergent and unified manner. This synthesis features the amide condensation of glycine-d-cysteine-containing segments with d-valine-containing segments for the direct assembly of the corresponding seco-acids, which are key precursors of macrolactones. The HDAC inhibition assay and cell-growth inhibition analysis of the synthesized analogues revealed novel aspects of their structure-activity relationship. This study demonstrated that simple modification at the C4 and C7 side chains in FK228 is effective for improving both HDAC inhibitory activity and isoform selectivity; moreover, potent and highly isoform-selective class I HDAC1 inhibitors were identified.

Efficacious anticancer drug delivery mediated by a pH-sensitive self-assembly of a conserved tripeptide derived from tyrosine kinase NGF receptor

We present herein a short tripeptide sequence (Lys-Phe-Gly or KFG) that is situated in the juxtamembrane region of the tyrosine kinase nerve growth factor (Trk NGF) receptors. KFG self-assembles in water and shows a reversible and concentration-dependent switching of nanostructures from nanospheres (vesicles) to nanotubes, as evidenced by dynamic light scattering, transmission electron microscopy, and atomic force microscopy. The morphology change was associated with a transition in the secondary structure. The tripeptide vesicles have inner aqueous compartments and are stable at pH 7.4 but rupture rapidly at pH≈6. The pH-sensitive response of the vesicles was exploited for the delivery of a chemotherapeutic anticancer drug, doxorubicin, which resulted in enhanced cytotoxicity for both drug-sensitive and drug-resistant cells. Efficient intracellular release of the drug was confirmed by fluorescence-activated cell sorting analysis, fluorescence microscopy, and confocal microscopy. Package for special delivery: A biologically active tripeptide self-assembles to produce nanovesicles at lower concentrations and nanotubes at higher concentrations (see scheme). The nanovesicles rupture at pH≈6 and are highly efficient in doxorubicin delivery to both drug-sensitive and drug-resistant cancer cells. This system is highly promising as a stimulus-responsive biocompatible nanovehicle. Copyright

Soluble tag-assisted peptide head-to-tail cyclization: Total synthesis of mahafacyclin B

A soluble tag-assisted liquid-phase method was successfully applied to peptide head-to-tail cyclization, leading to the total synthesis of antimalarial cyclic heptapeptide, mahafacyclin B (1). The cyclization was carried out in the liquid phase with the tag remaining, which allowed rapid reaction workup and product isolation.

N,O-isopropylidenated threonines as tools for peptide cyclization: Application to the synthesis of mahafacyclin B

(Chemical Equation Presented) The influence of a single N,O-isopropylidenated threonine turn-inducer on the cyclization of a linear heptapeptide precursor to mahafacyclin B has been investigated. Incorporation of an N,O-isopropylidenated threonine more th

Nickel complexes from α-amino amides as efficient catalysts for the enantioselective Et2Zn addition to benzaldehyde

Ni2+ complexes derived from simple α-amino amides catalyze very efficiently the addition of Et2Zn to benzaldehyde, giving (S)-1-phenylethanol as the major isomer in most cases (94% yield, 97% ee for R=Bn). The nature of the substituent on the amide nitrogen atom seems to play a key role in determining the asymmetric induction observed.

Phenylahistin and the phenylahistin analogs, a new class of anti-tumor compounds

A compound, its pharmaceutically acceptable salts, and/or its pro-drug esters, in isolated form, and methods for isolating, for formulating, and for administering the compound, salt, and/or pro-drug ester as an antitumor agent, wherein the compound, salt,