170848-34-7Relevant articles and documents
Readily available amino acid building blocks for the synthesis of phosphole-containing peptides
van Zutphen, Steven,Margarit, Vicente J.,Mora, Guilhem,Le Floch, Pascal
, p. 2857 - 2859 (2007)
Nucleophilic substitution of a phospholide anion onto protected 3-iodoalanine leads to the formation of an amino acid with an appended phosphole in excellent yield. Manipulation of the protecting groups, leads to building blocks suitable for the synthesis of phosphole-containing polypeptides.
Lanthanide triple helical complexes with a chiral ligand derived from 2,6-pyridinedicarboxylic acid
Muller,Schmidt,Jiricek,Hopfgartner,Riehl,Buenzli,Piguetf
, p. 2655 - 2662 (2001)
The ligand 3-[2,6-bis(diethylcarbamoyl)pyridine-4-yl]-N-(tert-butoxycarbonyl)alanine methyl ester (L4) bearing a chiral group in the 4-position of the pyridine ring has been synthesised and its interaction with trivalent lanthanide ions studied. L4 yields stable [Ln(L4)3]3+ complexes in acetonitrile, with logβ3 in the range 19-20. The specific rotary dispersion of the complexes is about ten times as large as that of the ligand alone, consistent with triple helical structures in solution. NMR data show the presence of only one time-averaged species in acetonitrile solution with a trigonal symmetry, that is, the helical P ? M interconversion is fast on the NMR time scale. Circularly polarised luminescence on the Eu and Tb triple helical complexes displays weak effects, pointing to only a small diastereomeric excess in solution. High resolution luminescence spectra of the Eu complex in the solid state reveal a local symmetry derived from a trigonal arrangement around the metal ion and the long 5D0 lifetime (1.58 ms) is indicative of the absence of water molecules bound in the inner co-ordination sphere. Energy transfer processes in the luminescent Eu and Tb triple helical complexes are discussed.
Z-selective olefin metathesis on peptides: Investigation of side-chain influence, preorganization, and guidelines in substrate selection
Mangold, Shane L.,Oleary, Daniel J.,Grubbs, Robert H.
, p. 12469 - 12478 (2014)
Olefin metathesis has emerged as a promising strategy for modulating the stability and activity of biologically relevant compounds; however, the ability to control olefin geometry in the product remains a challenge. Recent advances in the design of cyclom
Synthesis of d -abrines by palladium-catalyzed reaction of ortho-iodoanilines with N -Boc- N -methylalanyl-substituted acetaldehyde and acetylene
Danner, Paulami,Morkunas, Marius,Maier, Martin E.
, p. 2474 - 2477 (2013)
A novel strategy to N-Boc-N-methyl - tryptophans (abrine derivatives) was developed that relies on the palladium-catalyzed annulation of ortho-iodoanilines 12 with either N-Boc-N-methyl-propargylglycine 16 or aldehyde 11. Both 11 and 16 can be prepared from d-serine. An alternative route to propargylglycine 16 utilizes an enantioselective propargylation reaction of glycine imine 17.
Synthesis of C3-symmetric star-shaped molecules containing α-amino acids and dipeptides via Negishi coupling as a key step
Kotha, Sambasivarao,Todeti, Saidulu
, p. 371 - 377 (2019)
We demonstrate a new synthetic strategy toward star-shaped C3-symmetric molecules containing α-amino acid (AAA) derivatives and dipeptides. In this regard, trimerization and Negishi cross-coupling reactions are used as the key steps starting fr
Synthesis of orthogonally protected disulfide bridge mimetics
Tadd, Andrew C.,Meinander, Kristian,Luthman, Kristina,Wallen, Erik A. A.
, p. 673 - 675 (2011)
Concise routes to four orthogonally protected, enantiopure disulfide bridge mimetics are reported. These four dicarba analogues possess an alkyne, an (E)-alkene, a (Z)-alkene, and an alkane as substitutes for the disulfide bridge. Selective deprotection of one of these mimetics is also illustrated.
Nickel-Catalyzed Cross-Coupling of Amino-Acid-Derived Alkylzinc Reagents with Alkyl Bromides/Chlorides: Access to Diverse Unnatural Amino Acids
Gou, Fei-Hu,Ma, Ming-Jian,Wang, An-Jun,Zhao, Liang,Wang, Haoyang,Tong, Jie,Wang, Ze,Wang, Zhen,He, Chun-Yang
supporting information, p. 240 - 244 (2022/01/12)
Unnatural α-amino acids are important synthetic targets in the field of peptide science. Herein we report an efficient, versatile, and straightforward strategy for the synthesis of homophenylalanine derivatives via the nickel-catalyzed Csp3–Csp3 cross-coupling of (fluoro)benzyl bromides/chlorides with natural α-amino-acid-derived alkylzinc reagents. The current protocol features the advantages of a low-cost nickel catalyst system, synthetic convenience, and the tolerance of rich functionality and stereochemistry.
Efficient Hydro- and Organogelation by Minimalistic Diketopiperazines Containing a Highly Insoluble Aggregation-Induced, Blue-Shifted Emission Luminophore**
Molkenthin, Martin,Nachtsheim, Boris J.,Nau, Werner M.
, p. 16488 - 16497 (2021/10/25)
We report the synthesis, gelation abilities and aggregation-induced, blue-shifted emission (AIBSE) properties of two minimalistic diketopiperazine-based gelators. Despite containing a highly insoluble luminophore that makes up more than half of their respective molecular masses, efficient hydrogelation by multiple stimuli for one and efficient organogelation for the other compound are reported. Insights into the aggregation and gelation properties were gained through examination of the photophysical and material properties of selected gels, which are representative of the different modes of gelation. The synthesis of the gelators is highly modular and based on readily available amino acid building blocks, allowing the efficient and rapid diversification of these core structures and fine-tuning of gel properties.
ELONGATION FACTOR 1-ALPHA INHIBITORS AND USES THEREOF
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Paragraph 0551-0554; 0598-0603, (2021/08/13)
Disclosed herein, inter alia, are compounds for inhibiting Elongation Factor 1-alpha and uses thereof.
Synthesis and Biological Evaluation of a Library of AGE-Related Amino Acid Triazole Crosslinkers
Agelidis, Nektarios,Altevogt, Luca,Baro, Angelika,Bilitewski, Ursula,Bugdayci, Bakiye,Icik, Esra,Jolly, Anthony,L?ffler, Paul,Laschat, Sabine
supporting information, (2020/09/01)
Three N-Boc-protected amino acids, l-serine, l-aspartic, and l-glutamic acid, were either converted into their methyl azidoalkanoates or various alkynes via Bestmann-Ohira strategy or via reaction with propargylamine and propargyl bromide, respectively. The Cu-catalyzed click reaction provided a library of amino acid based triazoles, which were further N-methylated to triazolium iodides or deprotected and precipitated as free amino acid triazole dihydrochlorides. The biological properties of all derivatives were investigated by cytotoxicity assay (against L929 mouse fibroblasts) and broth microdilution method (E. coli ΔTolC and S. aureus). First results reveal complete inactivity for triazolium iodides with cell viabilities and microbial growths nearly 100 %, indicating them as possible analogs of advanced glycation endproducts (AGEs).
