Synthesis of chiral Nβ-protected amino diselenides from the corresponding amino alkyl iodides using NaBH2Se3 as a selenating reagent and their conversion to seleninic acids

Panguluri, Nageswara Rao; Panduranga, Veladi; Prabhu, Girish; Vishwanatha, T. M.; Sureshbabu, Vommina V.

doi:10.1039/c5ra06147d

Cited by 11 publications

(4 citation statements)

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“…Therefore, this compound can be prepared from selenocysteine derivative 600 in four steps as presented in Scheme 115. Hydrolysis of 604 affords the selenolated amino acids 599 , which proved to be very useful for peptide synthesis [447] . Thus, selenolated amino acids 599 is incorporated onto a solid‐supported polypeptide N ‐terminus as shown in Scheme 115 [444] .…”

Section: Selenium‐containing Peptidesmentioning

confidence: 99%

“…Hydrolysis of 604 affords the selenolated amino acids 599, which proved to be very useful for peptide synthesis. [447] Thus, selenolated amino acids 599 is incorporated onto a solid-supported polypeptide N-terminus as shown in Scheme 115. [444] Then, acidic cleavage from the resin and removal of the side-chain protecting groups by treatment with trifluoroacetic acid affords peptide 605 as a typical example.…”

Section: Selenium-containing Peptidesmentioning

confidence: 99%

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Organoselenium Compounds: Chemistry and Applications in Organic Synthesis

Sonego,

de Diego,

Szajnman

et al. 2023

Chemistry A European J

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Selenium, originally described as a toxin, turns out to be a crucial trace element for life that appears as selenocysteine and its dimer, selenocystine. From the point of view of drug developments, selenium‐containing drugs are isosteres of sulfur and oxygen with the advantage that the presence of the selenium atom confers antioxidant properties and high lipophilicity, which would increase cell membrane permeation leading to better oral bioavailability. In this article, we have focused on the relevant features of the selenium atom, above all, the corresponding synthetic approaches to access a variety of organoselenium molecules along with the proposed reaction mechanisms. The preparation and biological properties of selenosugars, including selenoglycosides, selenonucleosides, selenopeptides, and other selenium‐containing compounds will be treated. We have attempted to condense the most important aspects and interesting examples of the chemistry of selenium into a single article.

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Section: Selenium‐containing Peptidesmentioning

confidence: 99%

Section: Selenium-containing Peptidesmentioning

confidence: 99%

Organoselenium Compounds: Chemistry and Applications in Organic Synthesis

Sonego,

de Diego,

Szajnman

et al. 2023

Chemistry A European J

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“…Sureshbabu and co-workers 47 developed a convenient approach for the synthesis of N-protected L-selenocystine methyl esters 67 from the corresponding -iodoalanines 66 (obtained from N-protected L-Ser-OMe 65) using in situ generated NaBH 2 Se 3 as an efficient selenating reagent (Scheme 21). This new selenating agent operates under very mild reaction conditions, gives good yields in a short time and, importantly, the protocol is free of racemization.…”

Section: Short Review Synthesismentioning

confidence: 99%

Strategies for the Synthesis of Selenocysteine Derivatives

Oroz¹,

Avenoza²,

Busto³

et al. 2021

Synthesis

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β-Seleno-α-amino acids, known as selenocysteine (Sec) derivatives, have emerged as important targets because of their role in chemical biology, not only as part of selenoproteins with important redox properties, but also because of their activities as antivirals or metabolites effective in inhibiting carcinogenesis. In addition, there is a demand for this type of compounds due to their use in native chemical ligation to construct large peptides. Therefore, this review summarizes the various synthetic methods that have been published to construct Sec derivatives. Most of them involve the generation of the C-Se bond by nucleophilic substitution reactions, but other reactions such as radical or multicomponent strategies are also reported. Of particular importance is the Se-Michael addition of Se-nucleophiles to chiral bicyclic dehydroalanines, in which the stereogenic centre is generated under complete stereocontrol. 1 Introduction 2 Previously reviewed synthesis of Sec 3 Retrosynthesis of Sec derivatives 4 Sec derivatives by nucleophilic substitutions 5 Sec derivatives by radical processes 6 Sec derivatives by 1,4-conjugate additions

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“…21 Dialkyl diselenides are conveniently prepared through the reaction of tosylates or alkyl halides with the Se 2− ions generated in situ from selenium and a reducing agent in the presence of a base. 22–26 On the other hand, diaryl derivatives are typically obtained by the oxidation of selenol or selenolate formed by the treatment of aryllithium or arylmagnesium halide with elementary Se. 27,28 A route involving the solvolysis of arylselenocyanates prepared from the corresponding anilines has been recently described.…”

Section: Introductionmentioning

confidence: 99%