Category: 71989-31-6

Lubos, Marta published the artcileFunctional stapled fragments of human preptin of minimized length, Computed Properties of 71989-31-6, the publication is Organic & Biomolecular Chemistry (2022), 20(12), 2446-2454, database is CAplus and MEDLINE.

Preptin is a 34-amino-acid-long peptide derived from the E-domain of a precursor of insulin-like growth factor 2 (pro-IGF2) with bone-anabolic and insulin secretion amplifying properties. Here, we describe the synthesis, structures, and biol. activities of six shortened analogs of human preptin. Eight- and nine-amino-acid-long peptide amides corresponding to the C-terminal part of human preptin were stabilized by two types of staples to induce a higher proportion of helicity in their secondary structure. We monitored the secondary structure of the stapled peptides using CD. The biol. effect of the structural changes was determined afterwards by the ability of peptides to stimulate the release of intracellular calcium ions. We confirmed the previous observation that the stabilization of the disordered conformation of human preptin has a deleterious effect on biol. potency. However, surprisingly, one of our preptin analogs, a nonapeptide stabilized by olefin metathesis between positions 3 and 7 of the amino acid chain, had a similar ability to stimulate calcium ions’ release to the full-length human preptin. Our findings could open up new ways to design new preptin analogs, which may have potential as drugs for the treatment of diabetes and osteoporosis.

Organic & Biomolecular 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, Computed Properties of 71989-31-6.

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

Fujiwara, Daisuke published the artcileChemical Modification of Phage-Displayed Helix-Loop-Helix Peptides to Construct Kinase-Focused Libraries, COA of Formula: C20H19NO4, the publication is ChemBioChem (2021), 22(24), 3406-3409, database is CAplus and MEDLINE.

Conformationally constrained peptides hold promise as mol. tools in chem. biol. and as a new modality in drug discovery. The construction and screening of a target-focused library could be a promising approach for the generation of de novo ligands or inhibitors against target proteins. Here, we have prepared a protein kinase-focused library by chem. modifying helix-loop-helix (HLH) peptides displayed on phage and subsequently tethered to adenosine. The library was screened against aurora kinase A (AurA). The selected HLH peptide Bip-3 retained the ¦Á-helical structure and bound to AurA with a K_D value of 13.7 ¦ÌM. Bip-3 and the adenosine-tethered peptide Bip-3-Adc provided IC₅₀ values of 103 ¦ÌM and 7.7 ¦ÌM, resp., suggesting that Bip-3-Adc bivalently inhibited AurA. In addition, the selectivity of Bip-3-Adc to several protein kinases was tested, and was highest against AurA. These results demonstrate that chem. modification can enable the construction of a kinase-focused library of phage-displayed HLH peptides.

ChemBioChem 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, COA of Formula: C20H19NO4.

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

Peterse, Evert published the artcileSolid-phase synthesis of macrocyclic peptides via side-chain anchoring of the ornithine ¦Ä-amine, Recommanded Product: Fmoc-Pro-OH, the publication is European Journal of Organic Chemistry (2022), 2022(11), e202101341, database is CAplus.

Cyclic peptides represent a popular class of macrocyclic drug candidates and therefore their solid phase synthesis has attracted much attention. In this contribution we present an efficient method of side-chain anchoring for ornithine and lysine residues to be used in the standard Fmoc-based (Fmoc = 9-fluorenylmethoxycarbonyl) synthesis of cyclic peptides via on-resin cyclization. We demonstrate that the side chain of ornithine and lysine protected with N-Boc-group (Boc = tert-butoxycarbonyl) can efficiently be converted to the isocyanate which is then immobilized on Wang-type resin in almost quant. yield. We further show the synthesis of four biol. active cyclic peptides employing the side chain ornithine anchoring. Our method is at least on a par with the previously reported methodologies in terms of yield and the purity of the final products and is arguably operationally more straightforward.

European 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, Recommanded Product: Fmoc-Pro-OH.

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

Spears, Richard J. published the artcileA novel thiol-labile cysteine protecting group for peptide synthesis based on a pyridazinedione (PD) scaffold, HPLC of Formula: 71989-31-6, the publication is Chemical Communications (Cambridge, United Kingdom) (2022), 58(5), 645-648, database is CAplus and MEDLINE.

Herein we report a thiol-labile cysteine protecting group based on an unsaturated pyridazinedione (PD) scaffold. We establish compatibility of the PD in conventional solid phase peptide synthesis (SPPS), showcasing this in the on-resin synthesis of biol. relevant oxytocin. Furthermore, we establish the applicability of the PD protecting group towards both microwave-assisted SPPS and native chem. ligation (NCL) in a model system.

Chemical Communications (Cambridge, United Kingdom) 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 C11H21BF4N2O2, HPLC of Formula: 71989-31-6.

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

Ueda, Atsushi published the artcileE-Selective ring-closing metathesis in ¦Á-helical stapled peptides using carbocyclic ¦Á,¦Á-disubstituted ¦Á-amino acids, Related Products of catalysis-chemistry, the publication is Organic Letters (2022), 24(4), 1049-1054, database is CAplus and MEDLINE.

We present an E-selective ring-closing metathesis reaction in ¦Á-helical stapled peptides at positions i and i + 4. The use of two chiral carbocyclic ¦Á,¦Á-disubstituted ¦Á-amino acids, (1S,3S)-Ac₅c^3OAll and (1R,3S)-Ac₅c^3OAll, provides a high E-selectivity of a ¡Ü59:1 E:Z ratio, while mixtures with E:Z ratios of 2.1-0.5:1 were produced with standard acyclic (S)-(4-pentenyl)alanine amino acids. A stapled octapeptide composed of (1S,3S)- and (1R,3S)-Ac₅c^3OAll amino acids showed a right-handed ¦Á-helical crystal structure.

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 C3H5BN2O2, Related Products of catalysis-chemistry.

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

Kurnia, Dessy Yulyani published the artcileTotal synthesis of xylapeptide B [Cyclo-( L-Leu-L-Pro-N-Me-Phe-L-Val-D-Ala )], Product Details of C20H19NO4, the publication is Journal of Heterocyclic Chemistry (2022), 59(1), 131-136, database is CAplus.

Xylapeptide B is a cyclopentapeptide isolated from Xylaria sp. derived from the Chinese medicinal plant Sophora tonkinensis. Xylapeptide B was successfully synthesized by a combination of solid- and solution-phase, using the Fmoc (Fmoc = 9-fluorenylmethoxycarbonyl) strategy, and 2-chlorotrityl chloride resin. The coupling reagent used is a combination of HBTU/HOBt to assist in the formation of amide bonds. D-Ala was chosen as the C-terminal because it has a small residue and can facilitate the cyclization process. Linear peptide was cleaved from the resin using a dilute acid concentration of 20% TFA in DCM because the peptide has no protecting group at the side chain. Crude linear peptide was purified by semi-preparative RP-HPLC using 0%-100% ACN eluent for 35 min and obtained a pure mass of 22.4 mg (18.83%). Cyclization was carried out in solution phase using HBTU (3 equivalent) and DIPEA (1% volume/volume) in diluted concentration (1.25 mM) for 72 h at room temperature The cyclization stage was monitored by thin-layer chromatog. (TLC). Crude xylapeptide B was purified by semi-preparative RP-HPLC using 30%-80% ACN eluent for 40 min, to result in 6 mg (8.91%) of the desired xylapeptide B. All synthesized products were characterized by HR-TOFMS, ¹H-, and ¹³C-NMR.

Journal of Heterocyclic 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, Product Details of C20H19NO4.

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

Bisht, Babita published the artcileQuick Access to High-Purity Peptide Drugs Bradykinin, Leuprolide Analogue, 2(PZ-128), and Rapastinel with Minimal Reagents, Application In Synthesis of 71989-31-6, the publication is Journal of Organic Chemistry (2021), 86(24), 17667-17672, database is CAplus and MEDLINE.

Peptide drugs bradykinin, a leuprolide analog, 2(PZ-128), and rapastinel are synthesized in 56-77% yield using heating-assisted liquid-phase peptide synthesis on a soluble polynorbornene support. These drugs of com. utility and complex structures are obtained in 2-5.5 h with no epimerization and >95% purity using only 1.2 equiv of amino acids and coupling reagents. The peptide yield and purity are comparable or superior to the reported methods.

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, Application In Synthesis of 71989-31-6.

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

Xie, Yihui published the artcileDevelopment of Fmoc-protected bis-amino acids toward automated synthesis of highly functionalized spiroligomers, Safety of Fmoc-Pro-OH, the publication is Organic Letters (2022), 24(18), 3421-3425, database is CAplus and MEDLINE.

We report the fluorenylmethoxycarbonyl (Fmoc) protection of functionalized bis-amino acid building blocks using a temporary Cu²⁺ complexation strategy, together with an efficient multikilogram-scale synthesis of bis-amino acid precursors. This allows the synthesis of stereochem. and functionally diverse spiroligomers utilizing solid-phase Fmoc/tBu (Fmoc = 9-fluorenylmethoxycarbonyl) chem. to facilitate the development of applications. Four tetramers were assembled on a semiautomated microwave peptide synthesizer. We determined their secondary structures with two-dimensional NMR spectroscopy.

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 C6H8N2, Safety of Fmoc-Pro-OH.

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

Benediktsdottir, Andrea published the artcileAntibacterial sulfonimidamide-based oligopeptides as type I signal peptidase inhibitors: Synthesis and biological evaluation, Quality Control of 71989-31-6, the publication is European Journal of Medicinal Chemistry (2021), 113699, database is CAplus and MEDLINE.

Oligopeptide boronates with a lipophilic tail are known to inhibit the type I signal peptidase in E. coli, which is a promising drug target for developing novel antibiotics. Antibacterial activity depends on these oligopeptides having a cationic modification to increase their permeation. Unfortunately, this modification is associated with cytotoxicity, motivating the need for novel approaches. The sulfonimidamide functionality has recently gained much interest in drug design and discovery, as a means of introducing chirality and an imine-handle, thus allowing for the incorporation of addnl. substituents. This in turn can tune the chem. and biol. properties, which are here explored. We show that introducing the sulfonimidamide between the lipophilic tail and the peptide in a series of signal peptidase inhibitors resulted in antibacterial activity, while the sulfonamide isostere and previously known non-cationic analogs were inactive. Addnl., we show that replacing the sulfonamide with a sulfonimidamide resulted in decreased cytotoxicity, and similar results were seen by adding a cationic sidechain to the sulfonimidamide motif. This is the first report of incorporation of the sulfonimidamide functional group into bioactive peptides, more specifically into antibacterial oligopeptides, and evaluation of its biol. effects.

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 C20H19NO4, Quality Control of 71989-31-6.

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

Pei, Jingyan published the artcileTransport, Stability, and In Vivo Hypoglycemic Effect of a Broccoli-Derived DPP-IV Inhibitory Peptide VPLVM, Quality Control of 71989-31-6, the publication is Journal of Agricultural and Food Chemistry (2022), 70(16), 4934-4941, database is CAplus and MEDLINE.

Diabetes is a major metabolic disease that requires long-term pharmacotherapy. Bioactive peptides have unique advantages such as higher potency, selectivity, and safety over small mols. and have achieved great success in the treatment of diabetes. We previously isolated a dipeptidyl peptidase-IV (DPP-IV) inhibitory peptide VPLVM with IC₅₀ = 99.68¦ÌM from the protein hydrolyzates of broccoli stems and leaves. Here, we evaluated the interaction with DPP-IV, transport, stability, and in vivo hypoglycemic effects of VPLVM. VPLVM interacted closely and steadily with DPP-IV at S1 and S2 pockets. VPLVM had a good gastrointestinal enzyme resistance and was transported through the Caco-2 cell monolayer via paracellular diffusion and by the PepT1 with a P_app of 6.96 x 10^-7 cm/s. VPLVM has a t_1/2 of 12.56 ¡À 0.41 min in vitro plasma stability. In the oral glucose tolerance test, VPLVM showed an excellent hypoglycemic effect at 30 min after administration. VPLVM has potential as a candidate for the treatment of hyperglycemia.

Journal of Agricultural and Food 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