Anchoring of Fmoc amino acid to 4-alkoxybenzyl alcohol resin using a new esterification reagent

Akaji, Kenichi; Kuriyama, Naohiro; Kimura, Tooru; Fujiwara, Yoichi; Kiso, Yoshiaki

doi:10.1016/s0040-4039(00)79845-5

Cited by 42 publications

(12 citation statements)

References 14 publications

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“…Following a modified version of Kiso's procedure, [13] anion exchange of 1 was accomplished by treatment of KPF 6 in acetonitrile to afford chloroimidazolinium hexafluorophosphate 5. The reaction of 5 and sodium azide in acetonitrile and successive reprecipitation by using ether afforded 6 quantitatively.…”

Section: Resultsmentioning

confidence: 99%

Direct Synthesis of Organic Azides from Primary Amines with 2‐Azido‐1,3‐dimethylimidazolinium Hexafluorophosphate

et al. 2010

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Section: Resultsmentioning

confidence: 99%

Direct Synthesis of Organic Azides from Primary Amines with 2‐Azido‐1,3‐dimethylimidazolinium Hexafluorophosphate

et al. 2010

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“…For the ester bond formation to linkers such as the Wang resin and the HMPB resin it is necessary to use a base as catalyst, for which 4-dimethylaminopyridine is usually employed, with a carbodiimide as the carboxyl-activating reagent (Chan and White 2000). Other coupling reagents that furnish good yield for the esterification were also introduced, such as the chloro derivative 2-chloro, 1,3-dimethylimidazolidinium hexafluorophosphate (CIP) (Akaji et al 1992). For the very acid-labile 2-chlorotrityl chloride linker, the carboxyl group of the amino acid derivative attacks the methyl carbon and chloride is the leaving group, which leads to the linkage of Fmoc-amino acids to the 2-chlorotrityl chloride resin (Barlos et al 1989;James 1999).…”

Section: Coupling Of the First Amino Acid Derivative And Peptide Bondmentioning

confidence: 99%

Some Mechanistic Aspects on Fmoc Solid Phase Peptide Synthesis

Pires

Bemquerer

Nascimento

2013

Int J Pept Res Ther

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Peptides are biomolecules that may have several biological activities which makes them important to the environment in which they operate. Sometimes it is necessary for larger amounts of peptides to carry out some studies, like biological tests, NMR structural research or even interaction studies between peptides with other molecules. Expression can be an alternative for that. However, synthesis is specially useful when unnatural modifications or introduction of site specific tags are required. Synthetic peptides have been used for different studies such as cell signaling, development of epitope-specific antibodies, in cell-biology, biomarkers for diseases etc. Many different methodologies for peptide synthesis can be found in the literature. Solid phase peptide synthesis (SPPS) has been largely used and can be an excellent alternative to achieve larger quantities of these biomolecules. In this mini review, we aim to describe the SPPS and explain some of the mechanistic aspects and reagents involved in all phases of the synthesis: the use of resin, the ninhydrin test, some of the protecting groups, coupling reagents for peptide bond formation and the cleavage process.

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“…Then, catalytic hydrogenation, followed by the condensation of 5a-c with the corresponding isocyanates gave the desired urea derivatives 2c-s. Compound 2e was obtained by the condensation of 3 with 7 by using 2-chloro-1,3-dimethylimidazolidium hexafluorophosphate (CIP) 9,10) as a condensation reagent.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis of Potent and Selective Inhibitors against the Proliferation of Human Coronary Artery Smooth Muscle Cells.

Ogita

Isobe

Takaku

et al. 2003

CHEMICAL & PHARMACEUTICAL BULLETIN

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Proliferation of smooth muscle cells (SMCs) plays an important role in restenosis and in progression of atherosclerosis.2) Tranilast has been shown to inhibit platelet-derived growth factor (PDGF)-induced migration and proliferation in both SMCs 3) and endothelial cells (ECs). And the multicenter, randomized, double-blinded placebo-controlled trials demonstrated the potent preventive effect on restenosis after percutaneous transluminal coronary angioplasty (PTCA) in Japanese patients. 4,5) [at the phase III trial, 5) restenosis rate 18.8% (Tranilast 600 mg/d for 3 months, nϭ112) versus 44.1% (placebo, nϭ127); pϭ0.00005] But some patients had suffered liver dysfunction in these trials. We speculated that these frequent and severe side effects in these trials might have been caused by the high dose of Tranilast. In addition, the selective inhibitors of the proliferation of SMCs over that of ECs was more preferable for the treatment of restenosis than the non-selective inhibitors like Tranilast.6) So, we had been trying to search more potent and SMCs-selective compounds by modification of Tranilast.We previously reported a series of diarylamide derivatives, exhibiting potent and highly selective inhibition against SMCs proliferation induced by PDGF-BB. 7) We conducted that structure-activity relationship (SAR) study of the substituents at the A and B rings, and found potent inhibitor, 1a, which had about 30-fold stronger activity than Tranilast. In that case, the linker between A and B rings was not so influenced on the inhibitory activities (1a-c). In order to find more potent inhibitor, we also reported that the introduction of a ureido group to the B ring of our diarylamide derivatives make the inhibitory activity more potent and keep the selectivity for SMCs and 2b showed the most potent inhibitory activity for SMCs (IC 50 = 40 nM), which was 20-and 600-fold stronger than 1a and Tranilast respectively. 8) On the basis of these results (Fig. 1), we tried to confirm the effect of the linker between these rings against the proliferation of SMCs. In this paper, we report the results of the further modification of these urea derivatives. ChemistryThe syntheses of desired urea derivatives 2c-s are outlined in Chart 1. The condensation of 3 8) with corresponding acid halides was performed in the presence of triethylamine to provide 4a-c. Acid halide 10 was prepared from 9 with thionyl chloride, which was obtained by the condensation of 8 with ethyl bromoacetate followed by basic hydrolysis. Then, catalytic hydrogenation, followed by the condensation of 5a-c with the corresponding isocyanates gave the desired urea derivatives 2c-s. Compound 2e was obtained by the condensation of 3 with 7 by using 2-chloro-1,3-dimethylimidazolidium hexafluorophosphate (CIP) 9,10) as a condensation reagent. BiologyA series of these compounds were evaluated for their inhibitory activities on PDGF-induced proliferation of human coronary artery SMCs and fetal bovine serum (FBS)-induced the proliferation of human coronary artery ECs. Inhibit...

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Anchoring of Fmoc amino acid to 4-alkoxybenzyl alcohol resin using a new esterification reagent

Cited by 42 publications

References 14 publications

Direct Synthesis of Organic Azides from Primary Amines with 2‐Azido‐1,3‐dimethylimidazolinium Hexafluorophosphate

Direct Synthesis of Organic Azides from Primary Amines with 2‐Azido‐1,3‐dimethylimidazolinium Hexafluorophosphate

Some Mechanistic Aspects on Fmoc Solid Phase Peptide Synthesis

Synthesis of Potent and Selective Inhibitors against the Proliferation of Human Coronary Artery Smooth Muscle Cells.

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