Category: 87694-50-6

Du, Xiao; Zhang, Hao-yang; Lei, Meng; Li, Zi-yuan; Zhu, Yong-qiang published their research in Journal of Chemical Research on February 29 ,2016. The article was titled 《An efficient preparation of novel epoxyketone intermediates for the synthesis of carfilzomib and its derivatives》.Safety of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide The article contains the following contents:

A novel and efficient preparation of epoxyketone intermediates for the synthesis of carfilzomib and its derivatives was developed. Compared to reported methods, this highly stereoselective, environmentally friendly, low-cost method can be used in scaling up the synthesis of carfilzomib and its derivatives In addition to this study using (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide, there are many other studies that have used (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Safety of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide) was used in this study.

(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6) belongs to amides. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole.Safety of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors. In primary and secondary amides, the presence of N–H dipoles allows amides to function as H-bond donors as well.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Formula: C13H26N2O4On October 27, 1992 ,《Proteolysis of an active site peptide of lactate dehydrogenase by human immunodeficiency virus type 1 protease》 was published in Biochemistry. The article was written by Tomaszek, Thaddeus A. Jr.; Moore, Michael L.; Strickler, James E.; Sanchez, Robert L.; Dixon, J. Scott; Metcalf, Brian W.; Hassell, Anne; Dreyer, Geoffrey B.; Brooks, Isobel. The article contains the following contents:

Muscle and heart lactate dehydrogenases (LDHs) of rabbit and pig are specifically cleaved at a single position by HIV-1 protease, resulting in the conversion of 36-kDa subunits of the oligomeric enzymes into 21- and 15-kDa protein bands as analyzed by SDS-PAGE. While the proteolysis was observed at neutral pH, it became more pronounced at pH 6.0 and 5.0. The time courses of the cleavage of the 36-kDa subunits were commensurate with the time-dependent loss of both quaternary structure and enzymic activity. These results demonstrated that deoligomerization of rabbit muscle LDH at acidic pH rendered its subunits more susceptible to proteolysis, suggesting that a partially denatured form of the enzyme was the actual substrate. Proteolytic cleavage of the rabbit muscle enzyme occurred at a decapeptide sequence, His-Gly-Trp-Ile-Leu*Gly-Glu-His-Gly-Asp (scissile bond denoted throughout by an asterisk), which constitutes a strand-loop element in the muscle and heart LDH structures and contains the active site histidyl residue His-193. The kinetic parameters Km, Vmax/KmEt, and Vmax/Et for rabbit muscle LDH and the synthetic decapeptide Ac-His-Gly-Trp-Ile-Leu*Gly-Glu-His-Gly-Asp-NH2 were nearly identical, suggesting that the decapeptide within the protein substrate is conformationally mobile, as would be expected for the peptide substrate in solution Insertion of part of this decapeptide sequence into bacterial galactokinase likewise rendered this protein susceptible to proteolysis by HIV-1 protease, and site-directed mutagenesis of this peptide in galactokinase revealed that the Glu residue at the P2′ was important to binding to HIV-1 protease. Crystallog. anal. of HIV-1 protease complexed with a tight-binding peptide analog inhibitor derived from this decapeptide sequence revealed that the strand-loop structure of the protein substrate must adopt a β-sheet structure upon binding to the protease. The Glu residue in the P2′ position of the inhibitor likely forms hydrogen-bonding interactions with both the α-amide and γ-carboxylic groups of Asp-30 in the substrate-binding site. In the experiment, the researchers used (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Formula: C13H26N2O4)

(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6) belongs to amides.Formula: C13H26N2O4 The solubilities of amides and esters are roughly comparable. Typically amides are less soluble than comparable amines and carboxylic acids since these compounds can both donate and accept hydrogen bonds.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Tyrrell, Elizabeth; Brawn, Peter; Carew, Mark; Greenwood, Iain published an article on January 19 ,2011. The article was titled 《An expedient conversion of α-amino acids into Weinreb amides using COMU as a coupling agent》, and you may find the article in Tetrahedron Letters.Electric Literature of C13H26N2O4 The information in the text is summarized as follows:

The use of COMU, as a non-hazardous partner, in the coupling of N-Boc α-amino acids with N-methoxy-N-methylamine to afford the corresponding Weinreb amides is discussed. From a practical point of view the reaction can be monitored visually by virtue of the color change associated with the conversion of substrates (yellow) into the products (orange). As the byproducts of the reaction are conveniently water-soluble, the products are isolated relatively pure and with minimal racemization. These factors coupled with the short reaction time make this a very useful procedure. In the experiment, the researchers used (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Electric Literature of C13H26N2O4)

(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6) belongs to amides. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole. The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors.Electric Literature of C13H26N2O4 In primary and secondary amides, the presence of N–H dipoles allows amides to function as H-bond donors as well.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of C13H26N2O4On March 31, 1999, Llinares, M.; Devin, C.; Chaloin, O.; Azay, J.; Noel-Artis, A.-M.; Bernad, N.; Fehrentz, J.-A.; Martinez, J. published an article in Journal of Peptide Research. The article was 《Syntheses and biological activities of potent bombesin receptor antagonists》. The article mentions the following:

Bombesin receptor antagonists are potential therapeutic agents due to their ability to act as inhibitors of cellular proliferation. On the basis of our hypothesis concerning the mechanism of action of gastrin associating an activating enzyme to the receptor and on the results reported in the literature, we have synthesized bombesin analogs which have been modified in the C-terminal part. Potent bombesin receptor antagonists were obtained by replacement of Leu-13 with a statyl residue or with a residue bearing an hydroxyl group in place of the carbonyl function of Leu-13. Several inhibitors were able to recognize the bombesin receptor on rat pancreatic acini and antagonized bombesin stimulated amylase secretion in the nano-molar range. These compounds were also able to recognize the bombesin receptor and to inhibit [3H] thymidine incorporation in 3T3 cells with the same potency. The experimental process involved the reaction of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Electric Literature of C13H26N2O4)

(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6) belongs to amides.Electric Literature of C13H26N2O4 Amides include many other important biological compounds, as well as many drugs like paracetamol, penicillin and LSD. Low-molecular-weight amides, such as dimethylformamide, are common solvents.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Bohnstedt, Adolph C.; Prasad, J. V. N. Vara; Rich, Daniel H. published their research in Tetrahedron Letters on August 13 ,1993. The article was titled 《Synthesis of E- and Z-alkene dipeptide isosteres》.Name: (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide The article contains the following contents:

The syntheses of MeLeu-Leu and MeLeu-D-Leu alkene dipeptide isosteres (E)-I and (E)-II (Boc = Me3CO2C, R = H), and (Z)-I and (Z)-II (R = Me) are described. (E)-I and (E)-II were synthesized stereoselectively by employing the [2,3]-Wittig rearrangement to control double bond geometry and C-2 configuration. (Z)-I and (Z)-II were obtained as an easily separable mixture of diastereomers via alkylation of a Z-alkene MeLeu-Gly isostere that was obtained using a Z-selective Wittig reaction as the key step. All isosteres are isolated with high stereochem. purity. In the experimental materials used by the author, we found (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Name: (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide)

(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6) belongs to amides. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole.Name: (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors. In primary and secondary amides, the presence of N–H dipoles allows amides to function as H-bond donors as well.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Recommanded Product: 87694-50-6On May 6, 1998 ,《γ-Peptides forming more stable secondary structures than α-peptides. Synthesis and helical NMR-solution structure of the γ-hexapeptide analog of H-(Val-Ala-Leu)2-OH》 appeared in Helvetica Chimica Acta. The author of the article were Hintermann, Tobias; Gademann, Karl; Jaun, Bernhard; Seebach, Dieter. The article conveys some information:

For a comparison with the corresponding α- and β-hexapeptides H-(Val-Ala-Leu)2-OH (A) and H-(β-HVal-β-HAla-β-HLeu)2-OH (B), the corresponding γ-hexapeptide (I), built from the homochirally similar (S)-4-aminobutanoate, (R)-4-amino-5-methylhexanoate, and (R)-4-amino-6-methylheptanoate, was prepared The precursors were obtained either by double Arndt-Eistert homologation of protected Boc-Val-OH, Boc-Ala-OH, and Boc-Leu-OH, or by the superior route involving olefination/hydrogenation of the corresponding aldehydes, Boc-valinal, Boc-alaninal, and Boc-leucinal. Conventional peptide coupling (EDC/HOBt) furnished I through the intermediate γ-di- and γ-tripeptide. NMR measurements in (D5)pyridine and CD3OH solution (COSY, TOCSY, HSQC, HMBC, ROESY) reveal that I adopts a right-handed helical structure [(P)-2.61 helix of ∼5-Å pitch, containing 14-membered H-bonded rings] which is to be compared with the left-handed helix of β-peptide B [(M)-31 helix of 5-Å pitch, 14-membered H-bonded rings] and with the familiar right-handed, so-called α-helix of α-peptides [(P)-3.61 helix of 5.4-Å pitch, 13-membered rings]. Like the helix sense, the helix dipole reverses when going from α-(N→C) to β-(C→N) to γ-peptides (N→C). The surprising difference between the natural α-, and the analogous β- and γ-peptides is that the helix stability increases upon homologation of the residues. In the part of experimental materials, we found many familiar compounds, such as (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Recommanded Product: 87694-50-6)

(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6) belongs to amides. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole. The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors.Recommanded Product: 87694-50-6 In primary and secondary amides, the presence of N–H dipoles allows amides to function as H-bond donors as well.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Formula: C13H26N2O4On September 15, 2019 ,《Preparation and biological evaluation of soluble tetrapeptide epoxyketone proteasome inhibitors》 was published in Bioorganic & Medicinal Chemistry. The article was written by Lei, Meng; Zhang, Haoyang; Miao, Hang; Du, Xiao; Zhou, Hui; Wang, Jia; Wang, Xueyuan; Feng, Huayun; Shi, Jingmiao; Liu, Zhaogang; Shen, Jian; Zhu, Yongqiang. The article contains the following contents:

A series of novel tetrapeptidyl epoxyketone inhibitors of 20S proteasome was designed and synthesized. To fully understand the SAR, various groups at R1, R2, R3, R4 and R5 positions, including aromatic and aliphatic substituents were designed, synthesized and biol. assayed. Based on the enzymic results, seven compounds were selected to evaluate their cellular activities and soluble compound (I) showed strong potency against human multiple myeloma (MM) cell lines. Microsomal stability results indicated that compound I was more stable in mice, rat and human microsomes than marketed carfilzomib. The in vivo activities of this compound were evaluated with the xenograft mice models of MM cell lines ARH77 and RPMI-8226 with luciferase expression and the T/C value of the two models were 49.5% and 37.6%, resp. To evaluate the potential cardiovascular toxicity, inhibition of hERG ion channel in HEK293 cells by compound I and carfilzomib was carried out. The results indicated that I had no binding affinity for the hERG ion channel while carfilzomib could bind it with IC50 of 92.1 μM. The experimental part of the paper was very detailed, including the reaction process of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Formula: C13H26N2O4)

(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6) belongs to amides.Formula: C13H26N2O4 The solubilities of amides and esters are roughly comparable. Typically amides are less soluble than comparable amines and carboxylic acids since these compounds can both donate and accept hydrogen bonds.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

《An easy and convenient synthesis of Weinreb amides and hydroxamates》 was written by de Luca, Lidia; Giacomelli, Giampaolo; Taddei, Maurizio. Synthetic Route of C13H26N2O4 And the article was included in Journal of Organic Chemistry on April 6 ,2001. The article conveys some information:

A simple and convenient one-flask method for the preparation of Weinreb amides, hydroxamates, and hydroxamic acids on a large scale used mild reaction conditions and inexpensive reagents; the methodol. is a useful addition to parallel syntheses. Thus, reacting PhCO2H with MeNHOMe in THF containing 2-chloro-4,6-dimethoxy-1,3,5-triazine [CMDT], 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride [DMTMM], or cyanuric chloride and N-methylmorpholine [NMM] gave the amide PhCONMeOMe in high yields. The results came from multiple reactions, including the reaction of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Synthetic Route of C13H26N2O4)

(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6) belongs to amides.Synthetic Route of C13H26N2O4 Amides include many other important biological compounds, as well as many drugs like paracetamol, penicillin and LSD. Low-molecular-weight amides, such as dimethylformamide, are common solvents.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

《Copper(I)-mediated denitrogenative macrocyclization for the synthesis of cyclic α3β-tetrapeptide analogs》 was published in Chemistry – An Asian Journal in 2017. These research results belong to Chen, Chun-Chi; Wang, Sheng-Fu; Su, Yung-Yu; Lin, Yuya A.; Lin, Po-Chiao. Related Products of 87694-50-6 The article mentions the following:

A copper(I)-mediated denitrogenative reaction has been successfully developed for the preparation of cyclic tetrapeptides. The key reactive intermediate, ketenimine, triggers intramol. cyclization through attack of the terminal amine group to generate an internal β-amino acid with an amidine linkage. The chem. developed herein provides a new synthetic route for the preparation of cyclic α3β-tetrapeptide analogs that contain important biol. properties and results in rich structural information being obtained for conformational studies. With the success of this copper(I)-catalyzed macrocyclization, two histone deacetylase inhibitor analogs consisting of the cyclic α3β-tetrapeptide framework have been successfully synthesized. In addition to this study using (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide, there are many other studies that have used (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Related Products of 87694-50-6) was used in this study.

(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6) belongs to amides.Related Products of 87694-50-6 Amides include many other important biological compounds, as well as many drugs like paracetamol, penicillin and LSD. Low-molecular-weight amides, such as dimethylformamide, are common solvents.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Lee, Min Jae; Bhattarai, Deepak; Jang, Hyeryung; Baek, Ahreum; Yeo, In Jun; Lee, Seongsoo; Miller, Zachary; Lee, Sukyeong; Hong, Jin Tae; Kim, Dong-Eun; Lee, Wooin; Kim, Kyung Bo published their research in Journal of Medicinal Chemistry on August 12 ,2021. The article was titled 《Macrocyclic Immunoproteasome Inhibitors as a Potential Therapy for Alzheimer’s Disease》.Category: amides-buliding-blocks The article contains the following contents:

Previously, we reported that immunoproteasome (iP)-targeting linear peptide epoxyketones improve cognitive function in mouse models of Alzheimer’s disease (AD) in a manner independent of amyloid β. However, these compounds’ clin. prospect for AD is limited due to potential issues, such as poor brain penetration and metabolic instability. Here, we report the development of iP-selective macrocyclic peptide epoxyketones prepared by a ring-closing metathesis reaction between two terminal alkenes attached at the P2 and P3/P4 positions of linear counterparts. We show that a lead macrocyclic compound DB-60 (20) effectively inhibits the catalytic activity of iP in ABCB1-overexpressing cells (IC50: 105 nM) and has metabolic stability superior to its linear counterpart. DB-60 (20) also lowered the serum levels of IL-1α and ameliorated cognitive deficits in Tg2576 mice. The results collectively suggest that macrocyclic peptide epoxyketones have improved CNS drug properties than their linear counterparts and offer promising potential as an AD drug candidate. In the experimental materials used by the author, we found (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Category: amides-buliding-blocks)

(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6) belongs to amides.Category: amides-buliding-blocksAmides are pervasive in nature and technology. Proteins and important plastics like Nylons, Aramid, Twaron, and Kevlar are polymers whose units are connected by amide groups (polyamides); these linkages are easily formed, confer structural rigidity, and resist hydrolysis.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics