Sweet Selenium: Synthesis and Properties of Selenium-Containing Sugars and Derivatives

Abstract

In the last decades, organoselenium compounds gained interest due to their important biological features. However, the lack of solubility, which characterizes most of them, makes their actual clinical exploitability a hard to reach goal. Selenosugars, with their intrinsic polarity, do not suffer from this issue and as a result, they can be conceived as a useful alternative. The aim of this review is to provide basic knowledge of the synthetic aspects of selenosugars, selenonium salts, selenoglycosides, and selenonucleotides. Their biological properties will be briefly detailed. Of course, it will not be a comprehensive dissertation but an analysis of what the authors think is the cream of the crop of this interesting research topic.

On-water synthesis of glycosyl selenocyanate derivatives and their application in the metal free organocatalytic preparation of nonglycosidic selenium linked pseudodisaccharide derivatives

“…[11][12][13][14][15] Organoselenium chemistry has become an important topic of research due to the unique chemical behaviour of Se-containing compounds and their pharmacological potential. [16][17][18][19][20] Although, selenium has been incorporated in different classes of molecules to improve their therapeutic index, 21 the introduction of selenium within the carbohydrate framework has received less attention except for a few reports which include the synthesis of anomeric selenoglycosides [22][23][24][25][26][27] and their application in the preparation of oligosaccharides, [28][29][30] glycal derivatives, 31 glycosyl uorides, 32 C-glycosides 33 and medicinally useful compounds. 34 The synthesis of some cyclic sugar intermediates containing selenium in the ring has also been pursued.…”

“…6 A ); HRMS for C 56 H 56 O 13 Se [M + H] + : calcd 1017.2964; found: 1017tri-O-benzyl-6-deoxy-a-D-glucopyranosid-6-yl) selenide(19). Colorless oil; 1 H NMR (500 MHz, CDCl 3 ): d 8.00-7.25 (m, 30H, Ar-H), 6.13 (t, J ¼ 10.0 Hz, 1H, H-4 A ), 5.45 (t, J ¼ 10.0 Hz, 1H, H-3 A ),5.27 (dd, J ¼ 10.5 Hz, 3.5 Hz, 1H, H-2 A ),5.14 (d, J ¼ 3.5 Hz, 1H, H-1 A ),4.98 (d, J ¼ 11.0 Hz, 1H, PhCH), 4.92 (d, J ¼ 11.0 Hz, 1H, PhCH), 4.81 (d, J ¼ 11.0 Hz, 1H, PhCH), 4.73 (d, J ¼ 12.0 Hz, 1H, PhCH), 4.64 (d, J ¼ 12.5 Hz, 2H, 2 PhCH), 4.48 (d, J ¼ 3.5 Hz, 1H, H-1 B ), 4.26-4.22 (m, 1H, H-5 A ), 3.95 (t, J ¼ 9.0 Hz, 1H, H-4 B ), 3.83-3.80 (m, 1H, H-5 B ), 3.49 (s, 3H, OCH 3 ), 3.47-3.45 (m, 1H, H-2 B ), 3.36 (s, 3H, OCH 3 ), 3.34 (t, J ¼ 9.0 Hz, H-3 B ), 3.03 (d, J ¼ 12.5 Hz, 1H, H-6 aA ), 2.86 (d, J ¼ 5.5 Hz, 2H, H-6 abB ), 2.73 (dd, J ¼ 12.5 Hz, 5.0 Hz, 1H, H-6 bA ); 13 C NMR (125 MHz, CDCl 3 ): d 165.7, 165.6, 165.3 (3 PhCO), 138.7-127.5 (Ar-C), 97.6 (C-1 A ), 96.8 (C-1 B ), 81.8 (C-3 A ), 81.4 (C-4 A ), 80.1 (C-2 B ), 75.6, 75.1, 73.1 (3 PhCH 2 ), 72.9 (C-5 B ), 72.1 (C-2 A ), 71.5 (C-5 A ), 70.6 (C-3 B ), 70.2 (C-4 B ), 55.5, 55.0 (2 OCH 3 ), 26.8 (C-6 A ),25.6 (C-6 B ); HRMS for C 56 H 56 O 13 Se [M + H] + : calcd 1017.2964; found: 1017.2945.…”

Synthesis of Tetravalent Thio- and Selenogalactoside-Presenting Galactoclusters and Their Interactions with Bacterial Lectin PA-IL from Pseudomonas aeruginosa

“…Several selenium-containing carbohydrates are known from the literature. They were synthesized for various purposes [ 13 ], exploiting the inherent potential of the selenium nucleus [ 14 ]. Selenoglycosides were used as glycosyl donors [ 15 ], for protein glycoconjugation in site-selective glycosylation by Se-S-mediated ligation [ 16 ], as enzyme inhibitors ( O -GlcNAcase [ 17 ] and as novel glycosidase inhibitors [ 18 ]).…”

“…Our current aim is to synthesize the thio-and selenoglycoside analogues of the te valent lead-structure as well as their intermediate compounds to investigate their bind properties towards lectin PA-IL and the effect of sulfur and selenium on lectin bindi Several selenium-containing carbohydrates are known from the literature. They were s thesized for various purposes [13], exploiting the inherent potential of the selenium cleus [14]. Selenoglycosides were used as glycosyl donors [15], for protein glycoconju tion in site-selective glycosylation by Se-S-mediated ligation [16], as enzyme inhibitors GlcNAcase [17] and as novel glycosidase inhibitors [18]).…”

Masked Phenolic-Selenium Conjugates: Potent and Selective Antiproliferative Agents Overcoming P-gp Resistance

“…Organoselenium motifs have been combined with many other pharmacophores, like phenolic compounds [13,14], iminosugars [15], steroids [16,17], non-steroidal anti-inflammatory drugs [18], heterocycles [19][20][21], nucleosides [22], quinones [23], or metal coordination complexes [24] among others, or incorporated into the structures of natural products, like carbohydrates, giving access to the so called selenosugars [25]. The combination of chitosan and selenium nanoparticles has recently been reported as a vector for the transportation of mRNA for amplifying immune response in the potential development of cancer vaccines [26].…”