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A range of Nalpha-tetrachlorophthaloyl protected amino acids have been synthesized by an easy and efficient condensation procedure of the corresponding amino acid and tetrachlorophthaloyl anhydride under irradiation in an unmodified commercial microwave oven.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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2-Amino-4-pyrrolidinothieno[2,3-d]pyrimidine-6-carboxylic acid (4) (ATPC) is an unnatural amino acid with promise in applications as a building block for the synthesis of peptidomimetics. ATPC was obtained from both 3a and 3b thienopyrimidines by hydrolysis and hydrogenolysis, respectively. The synthesis of eleven ATPC-amino acids and two ATPC-peptides is described. ATPC is incorporated as N-terminal moiety in solution or solid-phase peptide synthesis using Boc or Fmoc methodology and without protection of the ATPC amino group. Georg Thieme Verlag Stuttgart.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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The solid phase synthesis of an amidated somatostatin analogue based on the principle of differentiated acidolysis is described.The acid labile and smoothly cleavable t-Bumeoc moiety (1percent TFA/DCM) is used for temporary Nalpha-protection of D- and L-amino acids and <4-<<<9H-fluoren-9-yl-methoxycarbonyl>amino>(4-methoxyphenyl)methyl>-2-methylphenoxy>acetic acid, attached to an aminomethylated polystyrene resin is used as acid sensitive linker of the solid carrier which releases the peptide in its amide form by treatment with TFA.Its preparation is described in detail.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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Five peptides of general structure X-Ser-Pro-Thr-Ser-Pro-Ser-Y (X = Tyr, quinoxaline2-carbonyl, acridine-9-carbonyl, Y = Tyr, (quinoxalin-2-yl)amino) were prepared using standard solid-phase peptide synthesis technique. Their interaction with DNA (calf thymus DNA and plasmids pUC9, pDeltaNS and pGEMEX) was studied using UV and CD spectroscopy, sedimentation analysis and agarose gel electrophoresis after treatment with topoisomerase 1. ln contrast to earlier findings (Suzuki M.: Nature 1990, 344, 562) intercalation into DNA structure has not been proved for any compound studied.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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For efficient peptide synthesis on a glass chip, 20 kinds of pentafluorophenyl (Pfp) esters of nitroveratryloxycarbonyl (NVOC)-protected amino acids were synthesized by using Pfp trifluoroacetate. Simple purification step gave moderate to high yield. The first loading time of each amino acid on glass surface was 30-60 min. The UV cleavage of the NVOC group was completed within 10 minutes. Georg Thieme Verlag Stuttgart – New York.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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We report broad guidance on how to catalyze enantioselective aldehyde additions to nitroalkene or maleimide Michael electrophiles in the presence of unprotected acidic spectator groups, e.g., carboxylic acids, acetamides, phenols, catechols, and maleimide NH groups. Remarkably, these l-threonine and l-serine potassium salt-catalyzed reactions proceed even when the nucleophilic and electrophilic Michael partners simultaneously contain acidic spectator groups. These findings begin to address the historical non-compatibility of enantioselective catalytic reactions in the presence of acidic moieties and simultaneously encroach on the spectator group tolerances normally associated with cellular environments. A carboxylate salt bridge, from the catalyst enabled enamine to the Michael electrophile, is thought to facilitate the expanded Michael substrate profile. A practical outcome of these endeavours is a new synthetic route to (R)-Pristiq, (?)-O-desmethylvenlafaxine, an antidepressant, in the highest yield known to date because no protecting groups are required. (Figure presented.).

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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Solid-phase peptide synthesis in water. Part 3: A water-soluble N-protecting group, 2-[phenyl(methyl)sulfonio]ethoxycarbonyl tetrafluoroborate, and its application to solid phase peptide synthesis in water

Chemical synthesis of peptides has been performed in various organic solvents, but the safe disposal of organic solvents is now an important environmental issue. Our aim is to be able to perform solid-phase peptide synthesis in water. For this, we have designed a new water-soluble N-protecting group, 2-[phenyl(methyl)sulfonio]ethoxycarbonyl (Pms), and have studied its introduction onto amino acids. Pms-amino acids were prepared by treating 2-(phenylthio)ethoxycarbonyl amino acids with methyl iodide in the presence of silver tetrafluoroborate. Because sulfur-containing amino acids, such as Met and Cys, were modified by the reaction, we designed a new reagent, 2-[phenyl(methyl)sulfonio]ethyl-4-nitrophenyl carbonate, to introduce the Pms group on amino acids. This reagent is a stable crystalline material and its introduction onto amino acids (including sulfur-containing amino acids) was successful. The solid-phase synthesis of Leu- and Met-enkephalin amides using Pms-protected amino acids was successfully achieved in water.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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Positron emission tomography evaluation of somatostatin receptor targeted 64Cu-TATE-liposomes in a human neuroendocrine carcinoma mouse model

Targeted therapeutic and diagnostic nanocarriers functionalized with antibodies, peptides or other targeting ligands that recognize over-expressed receptors or antigens on tumor cells have potential in the diagnosis and therapy of cancer. Somatostatin receptors (SSTRs) are over-expressed in a variety of cancers, particularly neuroendocrine tumors (NETs) and can be targeted with somatostatin peptide analogs such as octreotate (TATE). In the present study we investigate liposomes that target SSTR in a NET xenograft mouse model (NCI-H727) by use of TATE. TATE was covalently attached to the distal end of DSPE-PEG 2000 on PEGylated liposomes with an encapsulated positron emitter 64Cu that can be utilized for positron emission tomography (PET) imaging. The biodistribution and pharmacokinetics of the 64Cu-loaded PEGylated liposomes with and without TATE was investigated and their ability to image NETs was evaluated using PET. Additionally, the liposome accumulation and imaging capability was compared with free radiolabelled TATE peptide administered as 64Cu-DOTA-TATE. The presence of TATE on the liposomes resulted in a significantly faster initial blood clearance in comparison to control-liposomes without TATE. PEGylated liposomes with or without TATE accumulated at significantly higher quantities in NETs (5.1 ¡À 0.3 and 5.8 ¡À 0.2 %ID/g, respectively) than the free peptide 64Cu-DOTA- TATE (1.4 ¡À 0.3 %ID/g) 24 h post-injection. Importantly, 64Cu-loaded PEGylated liposomes with TATE showed significantly higher tumor-to-muscle (T/M) ratio (12.7 ¡À 1.0) than the control-liposomes without TATE (8.9 ¡À 0.9) and the 64Cu-DOTA-TATE free peptide (7.2 ¡À 0.3). The higher T/M ratio of the PEGylated liposomes with TATE suggests some advantage of active targeting of NETs, although no absolute benefit in tumor accumulation over the non-targeted liposomes was observed. Collectively, these data showed that 64Cu-loaded PEGylated liposomes with TATE conjugated to the surface could be promising new imaging agents for visualizing tumor tissue and especially NETs using PET.

Sometimes chemists are able to propose two or more mechanisms that are consistent with the available data. Quality Control of: H-Thr(tBu)-OH, If a proposed mechanism predicts the wrong experimental rate law, however, the mechanism must be incorrect.Welcome to check out more blogs about 4378-13-6, in my other articles.

Reference£º
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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A mild removal of Fmoc group using sodium azide

A mild method for effectively removing the fluorenylmethoxycarbonyl (Fmoc) group using sodium azide was developed. Without base, sodium azide completely deprotected Nalpha-Fmoc-amino acids in hours. The solvent-dependent conditions were carefully studied and then optimized by screening different sodium azide amounts and reaction temperatures. A variety of Fmoc-protected amino acids containing residues masked with different protecting groups were efficiently and selectively deprotected by the optimized reaction. Finally, a biologically significant hexapeptide, angiotensin IV, was successfully synthesized by solid phase peptide synthesis using the developed sodium azide method for all Fmoc removals. The base-free condition provides a complement method for Fmoc deprotection in peptide chemistry and modern organic synthesis. Graphical Abstract: [Figure not available: see fulltext.]

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Reference£º
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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Studies on 2-Aziridinecarboxylic Acid. VI. Synthesis of beta-Alkoxy-alpha-Amino Acids via Ring-opening Reaction of Aziridine

The reaction of aziridine derivatives having a urethane-type protecting group with several alcohols in the presence of boron trifluoride etherate afford the corresponding optically pure O-alkylserine and O-alkylthreonine derivatives via a ring-opening reaction of aziridine in good yield.

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Reference£º
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI