1095-85-8Relevant articles and documents
A sulfanyl-PEG derivative of relaxin-like peptide utilizable for the conjugation with KLH and the antibody production
Katayama, Hidekazu,Mita, Masatoshi
, p. 3596 - 3602 (2016)
A small peptide–keyhole limpet hemocyanin (KLH) conjugate is generally used as an antigen for producing specific antibodies. However, preparation of a disulfide-rich heterodimeric peptide–KLH conjugates is difficult. In this study, we developed a novel method for preparation of the conjugate, and applied it to the production of specific antibodies against the relaxin-like gonad-stimulating peptide (RGP) from the starfish. In this method, a sulfanyl group necessary for the conjugation with KLH was site-specifically introduced to the peptide after regioselective disulfide bond formation reactions. Using the conjugate, we could obtain specific antibodies with a high antibody titer. This method might also be useful for the production of antibodies against other heterodimeric peptides with disulfide cross-linkages, such as vertebrate relaxins.
Sulfur-Switch Ugi Reaction for Macrocyclic Disulfide-Bridged Peptidomimetics
Vishwanatha, Thimmalapura M.,Bergamaschi, Enrico,D?mling, Alexander
, p. 3195 - 3198 (2017)
A general strategy is introduced for the efficient synthetic access of disulfide linked artificial macrocycles via a Ugi four-component reaction (U4CR) followed by oxidative cyclization. The double-mercapto input is proposed for use in the Ugi reaction, thereby yielding all six topologically possible combinations. The protocol is convergent and short and enables the production of novel disulfide peptidomimetics in a highly general fashion.
Bulky toroidal and vesicular self-assembled nanostructures from fullerene end-capped rod-like polymers
Mazzier,Mba,Zerbetto,Moretto
, p. 4571 - 4574 (2014)
In this work, we present novel fullerene (C60) end-capped rod-like polypeptide-polymers, obtained by one-pot thiol-ene chemistry. These systems are able to self-assemble in water creating precise bulky microstructures of toroidal or vesicular shapes. Independent molecular dynamics simulations supported the observed experimental results. the Partner Organisations 2014.
Redox-responsive flower-like micelles of poly(l-lactic acid)-b-poly(ethylene glycol)-b-poly(l-lactic acid) for intracellular drug delivery
Yang, Qinglai,He, Changyu,Zhang, Zhen,Tan, Lianjiang,Liu, Bingya,Zhu, Zhenggang,Shao, Zhifeng,Gong, Bing,Shen, Yu-Mei
, p. 351 - 362 (2016)
Redox-responsive micelles self-assembled from triblock copolymers of poly(l-lactic acid)-poly(ethylene glycol)-poly(l-lactic acid) (PLA-PEG-PLA) with double-disulfide linkage in the backbone were synthesized and characterized by proton nuclear magnetic resonance (1H NMR) and size exclusion chromatography (SEC), in which both PEG (Mn = 1000, 2000 and 4000 g mol-1) and PLA (Mn = 1600 g mol-1) have different molecular weights respectively. The triblock copolymers PLA3000-PEG2000-PLA3000 and PLA3000-PEG4000-PLA3000 can self-assemble into flower-like micelles in aqueous media with average diameters 110 nm and 43 nm and lower critical micelle concentrations (CMC) 0.017 and 0.014 mg mL-1 respectively compared with that of diblock copolymers. Moreover, in vitro drug release analyses indicated that reductive environment can result in triggered drug release profiles. 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl- 2-H-tetrazolium bromide (MTT) assay in vitro showed no significant cytotoxicity as NIH 3T3 cells incubated in the micelles even when the concentrations up to 1000 μg/mL. Additionally fluorescence microscopy measurements and MTT assay demonstrated that the micelles exhibited a faster drug release and higher cellular proliferation inhibition due to the effect of intracellular reduction responsiveness compared with that of diblock copolymers. The above results suggest that the reduction-responsive, biodegradable and biocompatibility micelles could provide a platform to construct potential drug delivery systems for cancer therapy.
Clickable Nucleic Acids: Sequence-Controlled Periodic Copolymer/Oligomer Synthesis by Orthogonal Thiol-X Reactions
Xi, Weixian,Pattanayak, Sankha,Wang, Chen,Fairbanks, Benjamin,Gong, Tao,Wagner, Justine,Kloxin, Christopher J.,Bowman, Christopher N.
, p. 14462 - 14467 (2015)
Synthetic polymer approaches generally lack the ability to control the primary sequence, with sequence control referred to as the holy grail. Two click chemistry reactions were now combined to form nucleobase-containing sequence-controlled polymers in simple polymerization reactions. Two distinct approaches are used to form these click nucleic acid (CNA) polymers. These approaches employ thiol-ene and thiol-Michael reactions to form homopolymers of a single nucleobase (e.g., poly(A)n) or homopolymers of specific repeating nucleobase sequences (e.g., poly(ATC)n). Furthermore, the incorporation of monofunctional thiol-terminated polymers into the polymerization system enables the preparation of multiblock copolymers in a single reaction vessel; the length of the diblock copolymer can be tuned by the stoichiometric ratio and/or the monomer functionality. These polymers are also used for organogel formation where complementary CNA-based polymers form reversible crosslinks.
One-Pot Cyclization and Cleavage of Peptides with N-Terminal Cysteine via the N,S-Acyl Shift of the N-2-[Thioethyl]glycine Residue
Dziadecka, Anna,Stefanowicz, Piotr,Waliczek, Mateusz,Wierzbicka, Magdalena
, p. 12292 - 12299 (2021)
We developed a one-pot method for peptide cleavage from a solid support via the N,S-acyl shift of N-2-[thioethyl]glycine and transthioesterification using external thiols to produce cyclic peptides through native chemical self-ligation with the N-terminal
Practical fluorescence detection of acrolein in human plasma via a two-step tethering approach
Togashi, Masataka,Terai, Takuya,Kojima, Hirotatsu,Hanaoka, Kenjiro,Igarashi, Kazuei,Hirata, Yasunobu,Urano, Yasuteru,Nagano, Tetsuo
, p. 14946 - 14948 (2014)
Acrolein, a cytotoxic α,β-unsaturated aldehyde and disease biomarker, was determined in plasma by means of a novel tethering strategy using Michael addition of the compound to a fluorescent dye, followed by immobilization of the product on microbeads via
Expeditious and practical synthesis of tertiary alcohols from esters enabled by highly polarized organometallic compounds under aerobic conditions in Deep Eutectic Solvents or bulk water
Quivelli, Andrea F.,D'Addato, Giovanna,Vitale, Paola,García-álvarez, Joaquín,Perna, Filippo M.,Capriati, Vito
, (2021/01/18)
An efficient protocol was developed for the synthesis of tertiary alcohols via nucleophilic addition of organometallic compounds of s-block elements (Grignard and organolithium reagents) to esters performed in the biodegradable choline chloride/urea eutectic mixture or in water. This approach displays a broad substrate scope, with the addition reaction proceeding quickly (20 s reaction time) and cleanly, at ambient temperature and under air, straightforwardly furnishing the expected tertiary alcohols in yields of up to 98%. The practicability of the method is exemplified by the sustainable synthesis of some representative S-trityl-L-cysteine derivatives, which are a potent class of Eg5 inhibitors, also via telescoped one-pot processes.
Engineering Catalysts for Selective Ester Hydrogenation
Dub, Pavel A.,Batrice, Rami J.,Gordon, John C.,Scott, Brian L.,Minko, Yury,Schmidt, Jurgen G.,Williams, Robert F.
, p. 415 - 442 (2020/03/04)
The development of efficient catalysts and processes for synthesizing functionalized (olefinic and/or chiral) primary alcohols and fluoral hemiacetals is currently needed. These are valuable building blocks for pharmaceuticals, agrochemicals, perfumes, and so forth. From an economic standpoint, bench-stable Takasago Int. Corp.'s Ru-PNP, more commonly known as Ru-MACHO, and Gusev's Ru-SNS complexes are arguably the most appealing molecular catalysts to access primary alcohols from esters and H2 (Waser, M. et al. Org. Proc. Res. Dev. 2018, 22, 862). This work introduces economically competitive Ru-SNP(O)z complexes (z = 0, 1), which combine key structural elements of both of these catalysts. In particular, the incorporation of SNP heteroatoms into the ligand skeleton was found to be crucial for the design of a more product-selective catalyst in the synthesis of fluoral hemiacetals under kinetically controlled conditions. Based on experimental observations and computational analysis, this paper further extends the current state-of-the-art understanding of the accelerative role of KO-t-C4H9 in ester hydrogenation. It attempts to explain why a maximum turnover is seen to occur starting at 25 mol % base, in contrast to only 10 mol % with ketones as substrates.
