Activation of carboxylic acids by pyrocarbonates. Application of di-tert-butyl pyrocarbonate as condensing reagent in the synthesis of amides of protected amino acids and peptides

Pozdnev, V. F.

doi:10.1016/0040-4039(95)01412-b

Cited by 71 publications

(49 citation statements)

References 9 publications

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“…The amide 2 was obtained following Pozdnev's method [22] from Fmoc-Arg(Pbf)-OH (1) and converted into thioamide 3 by Lawesson's reagent [23]. Cyclocondensation of 3 with 3-bromo-oxo-propionic acid [24] leads to 4 in 82% yield.…”

Section: Resultsmentioning

confidence: 99%

“…]-undec-7-ene, CCl 4 , acetonitrile and pyridine [21]. Fmoc-Arg (Pbf)-OH (3.24 g, 5 mmol) (1), pyridine (0.25 ml) and (Boc) 2 O (1.5 g, 6.5 mmol) were dissolved in dioxane (15 ml), and then ammonium hydrogencarbonate (0.5 g, 6.3 mmol) was added and the mixture was stirred for 16 h [22]. The reaction mixture was diluted with water (30 ml) and stirred until crystallization was completed.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of thiazole, imidazole and oxazole containing amino acids for peptide backbone modification

Stankova

Videnov²,

Golovinsky

et al. 1999

J. Peptide Sci.

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Novel 5-ring heterocyclic building blocks are synthesized. These can be incorporated into analogs of peptide antibiotics such as microcin B17, which is a potent DNA-gyrase inhibitor that exhibits eight thiazole and oxazole moieties. In particular, the syntheses of imidazole and bisoxazole amino acids as novel peptidomimetics are reported, this includes a new procedure for the oxidative conversion of the intermediates oxazoline, imidazoline as well as oxazole-oxazoline into the corresponding heteroaromatic compounds. A mixture of 1,8-diazabicyclo-[5.4.0.]-undec-7-ene carbon tetrachloride/acetonitrile and pyridine proved to be a very effective and mild agent.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of thiazole, imidazole and oxazole containing amino acids for peptide backbone modification

Stankova

Videnov²,

Golovinsky

et al. 1999

J. Peptide Sci.

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“…phenylalanine tetrazole -silica sorbent 2.2.1 Synthesis of N-fluorenylmethoxycarbonyl phenylalaninamide, 1 [14] To a 250 mL round-bottomed flask, N-fluorenylmethoxycarbonyl phenylalanine (10.0 g, 25 mmol), pyridine (1.25 mL), t-butoxycarbonyl anhydride (7.5 g, 32.5 mmol), NH 4 HCO 3 (2.5 g, 31.5 mmol), and 120 mL dioxane were added. The reaction was stirred at room temperature for 24 h. The reaction was quenched with water (50 mL) and stirred.…”

Section: Synthesis Of Immobilized A-aminomentioning

confidence: 99%

New α‐amino phenylalanine tetrazole ligand for immobilized metal affinity chromatography of proteins

Lei

Liu

Xiong

et al. 2008

J of Separation Science

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A new chelating compound has been developed for use in the immobilized metal affinity chromatographic (IMAC) separation of proteins. The bidentate ligand, alpha-amino phenylalanine tetrazole, 4, was synthesized via a five-step synthesis from N-fluorenylmethoxycarbonyl phenylalanine and then immobilized onto silica through the epoxide coupling procedure. The binding behavior of the resulting IMAC sorbent, following chelation with Zn2+ to a density of 183 micromol Zn2+ ions/g silica, was characterized by the retention of proteins in the pH range of 5.0-8.0, and by the adsorption behavior of lysozyme with frontal chromatography at pH 6.0 and 8.0. The prepared column showed the separation ability to four test proteins and the retention time of these proteins increased with an increase in pH. From the derived isotherms, the adsorption capacity, qm, for the binding of lysozyme to immobilized Zn2+-alpha-amino phenylalanine tetrazole-silica was found to be 1.21 micromol/g at pH 6.0 and 1.20 micromol/g sorbent at pH 8.0, respectively, whilst the dissociation constants KD at these pH values were 5.22x10(-6) and 3.49x10(-6) M, respectively, indicating that the lysozyme was retained more stable under alkaline conditions, although the binding capacity in terms of micromole protein per gram sorbent remained essentially unchanged.

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“…N-3-Pyridylidenemethylamine with succinic anhydride gave 3 0 -methylnicotine and 3 0 -carboxynicotine [11]. The 3 0 -, 4 0 -, and 5 0 -carboxynicotines were transformed into the corresponding amides, aminomethylnicotines, and hydroxymethylnicotines [12][13][14][15]. Most of the reactions were nonstereospecific and generated mixture of diastereoisomers; however, some procedures were stereospecific and gave specific enantiomers.…”

Section: Introductionmentioning

confidence: 99%

Racemic synthesis of 2′‐substituted nicotine analogs

Rouchaud

Kem

2011

Journal of Heterocyclic Chem

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The chemical and pharmacological properties of 2′‐substituted nicotines are poorly understood relative to other substituted nicotines. We developed a practical synthesis of the key intermediate (±)‐2′‐cyanonicotine using the Polonovski reaction. Alkylation of (±)‐2′‐cyanonicotine with Grignard reagents led to several 2′‐alkylnicotines; (±)‐2′‐aminomethylnicotine, (±)‐2′‐hydroxymethylnicotine, and (±)‐2′‐carbamoylnicotine were also synthesized. J. Heterocyclic Chem., (2012).

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Activation of carboxylic acids by pyrocarbonates. Application of di-tert-butyl pyrocarbonate as condensing reagent in the synthesis of amides of protected amino acids and peptides

Cited by 71 publications

References 9 publications

Synthesis of thiazole, imidazole and oxazole containing amino acids for peptide backbone modification

Synthesis of thiazole, imidazole and oxazole containing amino acids for peptide backbone modification

New α‐amino phenylalanine tetrazole ligand for immobilized metal affinity chromatography of proteins

Racemic synthesis of 2′‐substituted nicotine analogs

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