cas 24250-85-9, L-4-Iodophenylalanine | Articles data

Articles about 24250-85-9Total 32 be found

Article title
Article abstract
Author
Journal number and time
Download

PRODUCTION METHOD FOR RADIOLABELED ARYL COMPOUND
The invention relates to a method of producing the radiolabeled aryl compound (I) Ar—X, or a salt thereof, wherein X is 211At, 210At, 123I, 124I, 125I, or 131I. The method involves reacting the aryl boronic acid compound (II) Ar—Y, or a salt thereof, wherein Y is a borono group (—B(OH)2) or an ester group thereof, with a radionuclide selected from 211At, 210At, 123I, 124I, 125I and 131I, in the presence of an oxidizing agent selected from an alkali metal iodide, an alkali metal bromide, N-bromosuccinimide, N-chlorosuccinimide and hydrogen peroxide, in water.
-
Paragraph 0208

(2020/12/10)

Sequence Programming with Dynamic Boronic Acid/Catechol Binary Codes
The development of a synthetic code that enables a sequence programmable feature like DNA represents a key aspect toward intelligent molecular systems. We developed herein the well-known dynamic covalent interaction between boronic acids (BAs) and catechols (CAs) into synthetic nucleobase analogs. Along a defined peptide backbone, BA or CA residues are arranged to enable sequence recognition to their complementary strand. Dynamic strand displacement and errors were elucidated thermodynamically to show that sequences are able to specifically select their partners. Unlike DNA, the pH dependency of BA/CA binding enables the dehybridization of complementary strands at pH 5.0. In addition, we demonstrate the sequence recognition at the macromolecular level by conjugating the cytochrome c protein to a complementary polyethylene glycol chain in a site-directed fashion.
Hebel, Marco,Riegger, Andreas,Zegota, Maksymilian M.,Kizilsavas, G?nül,Ga?anin, Jasmina,Pieszka, Michaela,Lückerath, Thorsten,Coelho, Jaime A. S.,Wagner, Manfred,Gois, Pedro M. P.,Ng, David Y. W.,Weil, Tanja
supporting information
p. 14026 - 14031
(2019/10/11)

PENTAFLUOROPHOSPHATE DERIVATIVE, ITS USES AND AN APPROPRIATE MANUFACTURING METHOD
The invention relates to a pentafluorophosphate derivative according to general formula (I): or a pharmaceutically acceptable salt or solvate thereof. Thereby, R1 and R2 denote independently from each other H or F; R3 denotes H, an optionally substituted C1-C10 alkyl, an optionally substituted C3-C10 cycloalkyl, or an optionally substituted C6-C20 aryl, wherein a hydrocarbon chain of the alkyl, the cycloalkyl or the aryl can be interrupted by one or more oxygen, sulfur and/or nitrogen atoms; and M denotes any cation; with the proviso that at least one of R1 and R2 denotes F, if R3 denotes H. The invention further relates to uses of such a pentafluorophosphate derivative and to an appropriate manufacturing method.
-
Page/Page column 12

(2019/04/05)

Photoinduced Hydroxylation of Organic Halides under Mild Conditions
Presented in this paper is photoinduced hydroxylation of organic halides, providing a mild access to a range of functionalized phenols and aliphatic alcohols. These reactions generally proceed under mild reaction conditions with no need for a photocatalyst or a strong base and show a wide substrate scope as well as excellent functional group tolerance. This work highlights the unique role of NaI that allows a challenging transformation to proceed under mild reaction conditions.
Cai, Yue-Ming,Xu, Yu-Ting,Zhang, Xin,Gao, Wen-Xia,Huang, Xiao-Bo,Zhou, Yun-Bing,Liu, Miao-Chang,Wu, Hua-Yue
supporting information
p. 8479 - 8484
(2019/10/16)

Site-Selective Modification of α-Amino Acids and Oligopeptides via Native Amine-Directed γ-C(sp3)-H Arylation
Site-selective modification of chemically and biologically valuable α-amino acids and peptides is of great importance for biochemical study and pharmaceutical development. Few methods based on remote C(sp3)-H functionalization of aliphatic side-chains of peptides has been disclosed in recent years. In this report, we developed a novel approach for γ-C(sp3)-H and γ-/δ-C(sp2)-H arylation of α-amino acids with α-hydrogen by native amine-directed C-H functionalization and further realized the γ-C(sp3)-H arylation of N-terminally unprotected peptides.
Yuan, Feipeng,Hou, Zhen-Lin,Pramanick, Pranab K.,Yao, Bo
supporting information
p. 9381 - 9385
(2019/11/28)

Synthesis and Explosion Hazards of 4-Azido- l -phenylalanine
A reliable, scalable, cost-effective, and chromatography-free synthesis of 4-azido-l-phenylalanine beginning from l-phenylalanine is described. Investigations into the safety of the synthesis reveal that the Ullman-like Cu(I)-catalyzed azidation step does not represent a significant risk. The isolated 4-azido-l-phenylalanine product, however, exhibits previously undocumented explosive characteristics.
Richardson, Mark B.,Brown, Derek B.,Vasquez, Carlos A.,Ziller, Joseph W.,Johnston, Kevin M.,Weiss, Gregory A.
supporting information
p. 4525 - 4536
(2018/04/26)

A palladium and gold catalytic system enables direct access to O- and S-linked non-natural glyco-conjugates
Here we report a straightforward cross-coupling method for the synthesis of non-natural glycoamino acids from alkyne-bearing monosaccharides and p-iodophenylalanine. Pd/Au-catalyzed Sonogashira coupling is tolerant to both O- and S-glycosides without any epimerization. In addition, no racemization of the amino acid was observed allowing direct access to the homogeneous glyco-conjugate in a single step. Notably, this Pd/Au catalytic system presents enhanced catalytic activity than conventional Pd/Cu and Pd-only platforms, and it further enables the convergent synthesis of glycodipeptides.
Jeon, Min Ho,Mathew, Bijoy P.,Kuram, Malleswara Rao,Myung, Kyungjae,Hong, Sung You
supporting information
p. 11518 - 11524
(2016/12/18)

Synthesis of six phenylalanine derivatives and their cell toxicity effect on human colon cancer cell line HT-29
Some phenylalanine (Phe) derivatives had important roles in pharmacology and may be used as pharmaceutical materials and pharmaceutical intermediates. In order to understand the cell toxicity of phenylalanine derivatives, we synthesized L-4-bromo-phenylalanine (Brp), L-4-iodophenylalanine (Ip), L-4-nitro-phenylalanine (Np), L-4-sulfonic-phenylalanine (Sp), L-4-phosphophenylalanine (Pp) and L-4-amino-phenylalanine (Np). We used mass spectrometry (MS), Infrared Spectroscopy (IR) or hydrogen-1 nuclear magnetic resonance spectrum (1H-NMR), and high performance liquid chromatography (HPLC) to test the correction of these products, MTT assay and Hoechst 33258 staining to detect their cell toxic effect on human colon cancer cell HT-29 (HT-29 cells). The results showed that these products were correct and the cytotoxicity of Pp>Ip>Sp and Np>Brp, Ap almost had no effect on HT-29 cells. In addition, Pp, Ip and Sp induced cell apoptosis, the other three kinds of phenylalanine derivatives induced neither apoptosis nor necrosis.
Zhao, Qianyi,Xu, Ting,Li, Menghua,Yang, Ying,Hu, Haopeng,Wang, Shupei,Yan, Wenjuan,Chen, Ran,Zhang, Chunyan,Xu, Cunshuan
p. 466 - 470
(2015/06/22)

PROCESSES AND REAGENTS FOR MAKING DIARYLIODONIUM SALTS
This disclosure relates to processes and reagents for making diaryliodonium salts, which are useful for the preparation of fluorinated, iodinated, astatinated and radiofluorinated aromatic compounds.
-
Paragraph 0431

(2014/05/08)

Self-liganded Suzuki-Miyaura coupling for site-selective protein PEGylation
Building with PEGs: PEG-boronic acids, in the presence of simple Pd sources, are capable of acting as direct and effective Suzuki reagents in 70-98 % yield. When combined with non-natural amino acids, they allow efficient and direct, site-selective PEGylation of proteins at predetermined positions under biologically compatible conditions without the need for exogenous ligands.
Dumas, Anaelle,Spicer, Christopher D.,Gao, Zhanghua,Takehana, Tsuyoshi,Lin, Yuya A.,Yasukohchi, Tohru,Davis, Benjamin G.
supporting information
p. 3916 - 3921
(2013/05/22)

Rewriting the bacterial glycocalyx via Suzuki-Miyaura cross-coupling
Suzuki-Miyaura cross-coupling has been used to couple novel carbohydrate-based boronic acids, site-selectively, to the surface of E. coli at an unnatural amino acid. In this way, benign metal-catalyzed cellular switching allowed modulation of interactions with biomolecular partners via prokaryotic O-glycosylation mimics. The Royal Society of Chemistry 2013.
Spicer, Christopher D.,Davis, Benjamin G.
supporting information
p. 2747 - 2749
(2013/05/08)

C-Glycosyl amino acids through hydroboration-cross-coupling of exo-glycals and their application in automated solid-phase synthesis
O-Glycosylation is one of the most important post-translational modifications of proteins. The attachment of carbohydrates to the peptide backbone influences the conformation as well as the solubility of the conjugates and can even be essential for binding to specific ligands in cell-cell interactions or for active transport over membranes. This makes glycopeptides an interesting class of compounds for medical applications. To enhance the long-term availability of these molecules in vivo, the stabilization of the glycosidic bond between the amino acid residue and the carbohydrate is of interest. The described modular approach affords β-linked C-glycosyl amino acids by a sequence of Petasis olefination of glyconolactones, stereoselective hydroboration and a mild B-alkyl-Suzuki coupling reaction. The coupling products were transformed to C-glycosyl amino acid building-blocks suitable for solid-phase synthesis and successfully incorporated into a partial sequence of the tumor-associated MUC1-glycopeptide. The resulting C-glycopeptides are candidates for the development of long-term stable mimics of O-glycopeptide vaccines. Copyright
Koch, Stefan,Schollmeyer, Dieter,L?we, Holger,Kunz, Horst
supporting information
p. 7020 - 7041
(2013/07/05)

A simple, efficient, regioselective and one-pot preparation of N-hydroxy- and N-O-protected hydroxyindoles via cycloaddition of nitrosoarenes with alkynes. Synthetic scope, applications and novel by-products
The thermal reaction between nitrosoarenes and alkynes under alkylating conditions produces N-alkoxyindoles as the major products in moderate to good yields and excellent regioselectivity. Various electrophiles are used affording different N-O-protected hydroxyindoles in a multi-component fashion. Privileged acetylenic substrates used in reactions with substituted nitrosoarenes are arylalkynes or propiolates. Potentially bioactive compounds and other classes of highly functionalizable indole products were prepared. Reactions between o-carbomethoxy-nitrosoarenes and arylacetylenes provided tricyclic compounds containing an acylaziridine indoline skeleton.
Ieronimo, Gabriella,Mondelli, Alessandro,Tibiletti, Francesco,Maspero, Angelo,Palmisano, Giovanni,Galli, Simona,Tollari, Stefano,Masciocchi, Norberto,Nicholas, Kenneth M.,Tagliapietra, Silvia,Cravotto, Giancarlo,Penoni, Andrea
p. 10906 - 10920
(2014/01/06)

Synthesis of modified phenylalanine peptides by cross enyne metathesis and a diels-alder reaction as key steps
Modified phenylalanine-based di- and tripeptides have been efficiently assembled by cross enyne metathesis and a Diels-Alder reaction as key steps under mild conditions. In all cases, peptide integrity was preserved, no racemisation was observed, and good yields of modified peptides were obtained.
Kotha, Sambasivarao,Goyal, Deepti,Thota, Niranjan,Srinivas, Venu
experimental part
p. 1843 - 1850
(2012/05/04)

Synthesis and biological evaluation of novel amprenavir-based P1-substituted bi-aryl derivatives as ultra-potent HIV-1 protease inhibitors
A series of P1-substituted biaryl amprenavir derivatives was designed and synthesized. These compounds were evaluated for enzyme inhibition and antiviral activity in vitro. Several compounds showed highly efficient antiviral activity with EC50 values down to 0.10 nM, which are more potent than marketed HIV-1 protease inhibitors. Docking study indicated that 12c has similar binding mode to amprenavir with full occupancy in P1.
Yan, Jianwei,Huang, Ning,Li, Shukun,Yang, Liu-Meng,Xing, Weiqiang,Zheng, Yong-Tang,Hu, Youhong
scheme or table
p. 1976 - 1979
(2012/04/17)

Palladium-mediated cell-surface labeling
Benign C-C bond formation at various sites in cell-surface channels has been achieved through Suzuki-Miyaura coupling of genetically positioned unnatural amino acids containing aryl halide side chains. This enabled site-selective cell surface manipulation of Escherichia coli; the phosphine-free catalyst caused no cell death at required Pd loadings, suggesting future in vivo application of catalytic metal-mediated bond formation in more complex organisms.
Spicer, Christopher D.,Triemer, Therese,Davis, Benjamin G.
supporting information; experimental part
p. 800 - 803
(2012/03/07)

Palladium-mediated site-selective Suzuki-Miyaura protein modification at genetically encoded aryl halides
Site-specific genetic incorporation of unnatural p-halophenylalanine amino acid residues as 'tags' coupled with Pd(0)-mediated Suzuki-Miyuara 'modification' has been enabled by discovery of an effective small molecule palladium scavenger.
Spicer, Christopher D.,Davis, Benjamin G.
supporting information; experimental part
p. 1698 - 1700
(2011/04/17)

Synthesis and binding studies of two new macrocyclic receptors for the stereoselective recognition of dipeptides
We present here the design, synthesis, and analysis of a series of receptors for peptide ligands inspired by the hydrogen-bonding pattern of protein β-sheets. The receptors themselves can be regarded as strands 1 and 3 of a three-stranded β-sheet, with crosslinking between the chains through the 4-position of adjacent phenylalanine residues. We also report on the conformational equilibria of these receptors in solution as well as on their tendency to dimerize. 1H NMR titration experiments are used to quantify the dimerization constants, as well as the association constant values of the 1:1 complexes formed between the receptors and a series of diamides and dipeptides. The receptors show moderate levels of selectivity in the molecular recognition of the hydrogen-bonding pattern present in the diamide series, selecting the α-amino acid-related hydrogen-bonding functionality. Only one of the two cyclic receptors shows modest signs of enantioselectivity and moderate diastereoselectivity in the recognition of the enantiomers and diastereoisomers of the Ala-Ala dipeptide (DDG0 1 (DD-DL) = -1.08 kcal/mol and DDG0 1(DD-LD) = -0.89 kcal/mol). Surprisingly, the linear synthetic precursors show higher levels of stereoselectivity than their cyclic counterparts.
Castilla, Ana Maria,Ballester, Pablo,Conn, M. Morgan
supporting information; experimental part

(2010/07/18)

A protected l-bromophosphonomethylphenylalanine amino acid derivative (BrPmp) for synthesis of irreversible protein tyrosine phosphatase inhibitors
Protein tyrosine phosphatases (PTPs) are important therapeutic targets for medicinal chemists and biochemists. General strategies for the development of inhibitors of these enzymes are needed. Several modular strategies which rely on phosphotyrosine mimics are known for PTP inhibitors. Previous strategies include phosphonomethylphenylalanine (Pmp) derivatives which act as competitive inhibitors. Pmp amino acid derivatives have been used to develop specific inhibitors by incorporation into sequences recognized by the PTP of interest. We report the synthesis of a new phosphonotyrosine analog, l- phosphonobromomethylphenylalanine (BrPmp), which acts as an inhibitor of PTPs. The BrPmp derivative was prepared as an Fmoc-protected amino acid which can be used in standard solid phase peptide synthesis (SPPS) methods. The synthesis of the protected amino acid derivative requires 11 steps from tyrosine with a 30% overall yield. Enzyme inhibition studies with the PTP CD45 demonstrate that BrPmp derivatives are irreversible inhibitors of the enzyme. A tripeptide which incorporated BrPmp had increased inhibitory potency against PTP relative to BrPmp alone, confirming that the incorporation of BrPmp into peptide sequences provides additional context to improve enzyme binding.
Tulsi, Naresh S.,Downey, A. Michael,Cairo, Christopher W.
experimental part
p. 8679 - 8686
(2011/02/25)

Synthesis of novel N-protected hydrophobic phenylalanines and their application in potential antibacterials
An efficient synthesis of two new N-acetyl-4′-arylphenylalanines is described together with their incorporation into a number of cationic peptoid antibacterial agents, one of which had an MIC of 7.8 μg/mL against Staphylococcus aureus. Crown Copyright
Boyle, Timothy P.,Bremner, John B.,Coates, Jonathan A.,Deadman, John,Keller, Paul A.,Pyne, Stephen G.,Somphol, Kittiya
experimental part
p. 1001 - 1009
(2009/09/06)

Sonogashira and "click" reactions for the N-terminal and side-chain functionalization of peptides with [Mn(CO)3(tpm)] +-based CO releasing molecules (tpm = tris(pyrazolyl)methane)
A recently identified photoactivatable CO releasing molecule (CORM) based on [Mn(CO)3(tpm)]+ was conjugated to functionalized amino acids and model peptides using the Pd-catalyzed Sonogashira cross-coupling and the alkyne-azide 1,3-dipolar cycloaddition ("Click reaction"). Both were found to be fully compatible with all functional groups present. The CORM-peptide conjugates were isolated in reasonable yield and high purity, as indicated by IR spectroscopy, ESI mass spectrometry and RP-HPLC. The myoglobin assay was used to demonstrate that they have CO release properties identical those of the parent compound. This work thus opens the way for a targeted delivery of CORMs to cellular systems.
Pfeiffer, Hendrik,Rojas, Alfonso,Niesel, Johanna,Schatzschneider, Ulrich
supporting information; experimental part
p. 4292 - 4298
(2009/10/09)

PEPTIDIC COMPOUNDS
The present invention provides a compound of formula (I), (II), (III) and (IV) as defined herein and pharmaceutically acceptable derivatives thereof. The present invention further provides use of the compounds of the present invention in the treatment of bacterial infection and in the treatment of HIV infection. Also provided are pharmaceutical compositions comprising the compounds of the present invention.
-
Page/Page column 170-171

(2008/06/13)

Gram-scale preparation of a p-(C-glucopyranosyl)-L-phenylalanine derivative by a negishi cross-coupling reaction
A p-(C-glucopyranosyl)-L-phenylalanine derivative protected to be directly incorporated into a peptidic chain is prepared in 37 % yield from glucose on a gram scale, with a Negishi cross-coupling reaction as the key step. Zincated glucal and p-iodo-L-phenylalanine are involved in this organometallic coupling, which gives rise to a link between the sugar and amino acid moieties in 90 % yield; the β-gluco configuration of the C-glycopyranosyl amino acid is ascertained by a stereoselective hydroboration of the double bond of the glucal. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
Ousmer, Malika,Boucard, Valerie,Lubin-Germain, Nadege,Uziel, Jacques,Auge, Jacques
p. 1216 - 1221
(2007/10/03)

2-Alkoxydihydrocinnamates as PPAR agonists. Activity modulation by the incorporation of phenoxy substituents
Herein we describe a series of potent and selective PPARγ agonists with moderate PPARα affinity and little to no affinity for other nuclear receptors. In vivo studies in a NIDDM animal model (ZDF rat) showed that these compounds are efficacious at low doses in glucose normalization and plasma triglyceride reduction. Compound 1b (LY519818) was selected from our SAR studies to be advanced to clinical evaluation for the treatment of type II diabetes. Herein we describe a series of potent and selective PPARγ agonists with moderate PPARα affinity and little to no affinity for other nuclear receptors. In vivo studies in a NIDDM animal model (ZDF rat) showed that these compounds are efficacious at low doses in glucose normalization and plasma triglyceride reduction. Compound 1b (LY519818) was selected from our SAR studies to be advanced to clinical evaluation for the treatment of type II diabetes.
Martín, José A.,Brooks, Dawn A.,Prieto, Lourdes,González, Rosario,Torrado, Alicia,Rojo, Isabel,López De Uralde, Beatriz,Lamas, Carlos,Ferritto, Rafael,Dolores Martín-Ortega, María,Agejas, Javier,Parra, Francisco,Rizzo, John R.,Rhodes, Gary A.,Robey, Roger L.,Alt, Charles A.,Wendel, Samuel R.,Zhang, Tony Y.,Reifel-Miller, Anne,Montrose-Rafizadeh, Chahrzad,Brozinick, Joseph T.,Hawkins, Eric,Misener, Elizabeth A.,Briere, Daniel A.,Ardecky, Robert,Fraser, James D.,Warshawsky, Alan M.
p. 51 - 55
(2007/10/03)

Expanding the eukaryotic genetic code
This invention provides compositions and methods for producing translational components that expand the number of genetically encoded amino acids in eukaryotic cells. The components include orthogonal tRNAs, orthogonal aminoacyl-tRNA synthetases, orthogonal pairs of tRNAs/synthetases and unnatural amino acids. Proteins and methods of producing proteins with unnatural amino acids in eukaryotic cells are also provided.
-
(2008/06/13)

C-Glycosylated Phenylalanine Synthesis by Palladium-Catalyzed Cross-Coupling Reactions
A new and convergent synthesis of a C-glycosylated phenylalanine derivative using palladium-catalyzed Stille and Neghishi cross-coupling reactions is described. The coupling product constitutes a precursor of a natural glycosylated tyrosine mime.
Boucard, Valérie,Larrieu, Karen,Lubin-Germain, Nadège,Uziel, Jacques,Augé, Jacques
p. 1834 - 1837
(2007/10/03)

COMPOUNDS
The invention relates to compounds of formula (I) wherein R1 represents benzyl; R2 represents pyrazole; or a pharmaceutically acceptable derivative thereof. The invention also relates to pharmaceutical compositions containing compounds of formula (I) and to the use of compounds of formula (I) in medicine, particularly in the amelioration of a clinical condition for which a ACE and/or NEP inhibitor is indicated.
-
Page 19-20

(2010/02/04)

Metal control of non-polar binding shape selectivity
Ligand 1 forms a hydrophobic cavity upon binding to metals, the shape of which depends on the metal. A reversal in binding preference for naphthalene or biphenyl groups is found when the metal is changed from zinc to copper, with a selectivity change of 260 fold.
Wang, Fen,Schwabacher, Alan W.
p. 7641 - 7644
(2007/10/03)

Efficient Synthesis of a Phosphinate Bis-Amino Acid and Its Use in the Construction of Amphiphilic Peptides
A new amphiphilic bis-amino acid has been designed and its convergent, asymmetric synthesis achieved in differentially protected form.A convenient preparation of iodophenylalanine, a generally useful starting material, is disclosed.Sequential palladium-catalyzed couplings of aryl iodides to phosphinate lead directly to the target protected bis-amino acid.Controlled peptide coupling of the new bis-amino acid is also demonstrated.
Lei, Haiyan,Stoakes, Mark S.,Herath, Kamal P. B.,Lee, Jinho,Schwabacher, Alan W.
p. 4206 - 4210
(2007/10/02)

Self-assembly of a hydrophobic binding site
-
Schwabacher, Alan W.,Lee, Jinho,Lei, Haiyan
p. 7597 - 7598
(2007/10/02)

Protection of Functional Groups and Stannylation of Phenylalanine
The protection of both amino and carboxylic acid groups in p-halogenated phenylalanine was done by using different reagents.The protected amino acid was stannylated by using hexamethyldistannane in the presence of tetrakis(triphenylphosphine)palladium as catalyst.
Metwally, S. A.,Coenen, H. H.,Stoecklin, G.
p. 4437 - 4440
(2007/10/02)

Iodinated phenylalanines. Tests for selective localization in pancreas and preparation of 3,4,5-triiodophenylalanine.
-
Schatz,O'Brien,Sandusky
p. 140 - 142
(2007/10/06)