95581-07-0Relevant articles and documents
Synthesis of biurets: Via TMSNCO addition to 1-aminosugars: Application in the de novo synthesis of dC oxidation products
Tsoulougian, Veronika,Psykarakis, Emmanuel E.,Gimisis, Thanasis
, p. 973 - 981 (2019/02/01)
The reaction between 1-aminosugars and trimethylisocyanate (TMSNCO) was optimised as a one-step synthetic strategy for the synthesis of sugar biurets. This protocol was successfully applied to a number of 1-aminosugars, which exclusively provided the corresponding biurets in 67-99% yields. The new methodology was applied in the de novo synthesis of N1-(2-deoxy-α/β-d-erythro-pentofuranosyl)biuret (dfBU) and N1-(2-deoxy-α/β-d-erythro-pentopyranosyl)biuret (dpBU), two known DNA lesions arising from the hydroxyl radical induced decomposition of 2′-deoxycytidine (dCyd).
OLIGONUCLEOTIDE DERIVATIVE, OLIGONUCLEOTIDE CONSTRUCT USING THE SAME, AND METHODS FOR PRODUCING THEM
-
, (2018/04/19)
The oligonucleotide derivative of the present invention is represented by Formula (1). This derivative is considered to be introduced into cells by binding of its amino sugar chain moiety to a ligand on cell surfaces, and have selective drug delivery function. The oligonucleotide derivative can be easily synthesized and introduced into cells without using a lipofection reagent. wherein—A and B are independently modified or unmodified oligonucleotides whose total chain length is 3 or more, and A and B do not contain hydroxyl groups at 3′ and 5′ ends of the oligonucleotide; S represents a sugar substituent, a peptide chain, or a tocopherol-binding group; and an alkyl group may be bound instead of hydrogen bound to a benzene ring.
AuBr3-catalyzed azidation of per-O-acetylated and per-O-benzoylated sugars
Rajput, Jayashree,Hotha, Srinivas,Vangala, Madhuri
, p. 682 - 687 (2018/03/30)
Herein we report, for the first time, the successful anomeric azidation of per-O-acetylated and per-O-benzoylated sugars by catalytic amounts of oxophilic AuBr3 in good to excellent yields. The method is applicable to a wide range of easily accessible per-Oacetylated and per-O-benzoylated sugars. While reaction with per-O-acetylated and per-O-benzoylated monosaccharides was complete within 1-3 h at room temperature, the per-O-benzoylated disaccharides needed 2-3 h of heating at 55°C.
A rigid lanthanide binding tag to aid NMR studies of a 70 kDa homodimeric coat protein of human norovirus
Mallagaray, Alvaro,Domínguez, Gema,Peters, Thomas,Pérez-Castells, Javier
, p. 601 - 604 (2016/01/12)
Attachment of human noroviruses to histo blood group antigens is thought to be essential for infection of host cells. Molecular details of the attachment process can be studied in vitro using a variety of NMR experiments. The use of protein NMR based experiments requires assignments of backbone NMR signals. Using uniformly 2H,15N-labeled protruding domains (P-dimers) of a prevalent epidemic human norovirus strain (GII.4 Saga) we have studied the potential of α-l-fucose covalently linked to a rigid lanthanide binding tag to aid backbone assignments using the paramagnetic properties of lanthanide ions. The synthesis of tagged α-l-fucose is reported. Notably, the metal chelating unit connects to the carbohydrate via a triazole linker constructed using click chemistry.
Sugara-oligoamides: Synthesis of DNA minor groove binders
Badaea, Concepcion,Souard, Florence,Vicent, Cristina
, p. 10870 - 10881 (2013/02/22)
Sugar-oligoamides have been designed and synthesized as structurally simple carbohydrate-based ligands to study carbohydratea-minor groove DNA interactions. Here we report an efficient solution-phase synthetic strategy to obtain two broad families of sugara-oligoamides. The first type, structure vector A (-Py[Me]-γ-Py-Ind), has a methyl group present as a substituent on the nitrogen of pyrrole B, connected to the C terminal of the oligoamide fragment. The second type, structure vector B (-Py[(CH2) 11OH]-γ-Py-Ind), has an alkyl chain present on the nitrogen of pyrrole B connected to the C terminal of the oligoamide fragment and has been designed to access to di-and multivalent sugara-oligoamides. By using sequential DIPC/HOBt coupling reactions, the oligoamide fragment-Py[R]-γ-Py-Ind has been constructed. The last coupling reaction between the anomeric amino sugar and the oligoamide fragment was carried out by activating the acid derivative as a BtO-ester, which has been performed by using TFFH. The isolated esters (BtO-Py[R]-γ-Py-Ind) were coupled with selected amino sugars using DIEA in DMF. The synthesis of two different selective model vectors (vector A (1) and vector B (2)) and two types of water-soluble sugara-oligoamide ligands, with vector A structure (compounds 3a-7) and with vector B structure (compound 8), was carried out.
"click" synthesis of nonsymmetrical bis(1,2,3-triazoles)
Aizpurua, Jesus M.,Azcune, Itxaso,Fratila, Raluca M.,Balentova, Eva,Sagartzazu-Aizpurua, Malaien,Miranda, Jose I.
supporting information; experimental part, p. 1584 - 1587 (2010/06/16)
Chemical Fig. Repretation Unsymmetrically 1,1'-disubstituted 4,4'-bis-1 H-1,2,3-triazoles 4 have been prepared from 4-ethynyl-1,2,3-triazoles 5 and azides. Following a "double-click" strategy, two complementary approaches were implemented for the preparation of the key 4-ethynyltriazole Intermediates 5: (a) the stepwise Swern oxidatlon/Ohira-Bestman alkynylation of readily available 4-hydroxymethyl-1,2,3-triazoles 8 and (b) the stepwise cycloaddition of TMS-1,4-butadiyne 9. The method is highlighted by Its compatibility with orthogonally protected and functlonallzed saccharide-peptide hybrids and its ability to be extended to the trlsubstituted counterparts 12.
"Click" saccharide/β-lactam hybrids for lectin inhibition
Palomo, Claudio,Aizpurua, Jesus M.,Balentova, Eva,Azcune, Itxaso,Santos, J. Ignacio,Jimenez-Barbero, Jesus,Canada, Javier,Miranda, Jose Ignacio
supporting information; experimental part, p. 2227 - 2230 (2009/09/25)
(Figure Presented) Hybrid glycopeptide β-lactam mimetics designed to bind lectins or carbohydrate recognition domains in selectins have been prepared according to a "shape-modulating linker" design. This approach was implemented using the azide-alkyne "cl
Synthesis and activity of dipeptides, linked to targeting ligands, as specific NK cell enhancers
Abbott, Shaun D.,Gagnon, Lyne,Lagraoui, Mouna,Kadhim, Salam,Attardo, Giorgio,Zacharie, Boulos,Penney, Christopher L.
, p. 1909 - 1926 (2007/10/03)
Water soluble analogues of the lipophilic immunostimulant, octadecyl D- alanyl-L-glutamine, BCH-527, were synthesized and evaluated for the ability to stimulate natural killer (NK) cells. One of these compounds in which the octadecyl chain of BCH-527 was
Synthesis of glycosyl phosphates and azides
Sabesan,Neira
, p. 169 - 185 (2007/10/02)
Anomerically enriched diphenyl hexopyranosyl phosphate triesters have been prepared from O-alkyl and -acylated hexopyranoses, using diphenyl chlorophosphate and 4-N,N-dimethylaminopyridine. Glycosyl phosphate triesters of D-gluco-, D-galacto-, D-manno, 2-acetamido-2-deoxy-D-gluco-, L-fuco-, and L-rhamno-pyranosyl derivatives have been obtained by this procedure. At temperatures 0° and above, and under thermodynamic control, diphenyl glycosyl phosphates cis to the pyranosyl C-2 substituent are formed predominantly, whereas at low temperatures and under kinetic control, glycosyl phosphate triesters having 2-trans stereochemistry are obtained. The β-glycosyl phosphate triesters of D-glucose and D-galactose derivatives are unstable and undergo anomerization to the α-glycosyl phosphate triesters, in contrast to the stable β-phosphate derivatives of L-rhamnose and D-mannose. These phosphate triesters have been deprotected to glycosyl phosphate triethylammonium salts, suitable for the preparation of other key biological derivatives, such as nucleotide sugars. In addition, the diphenyl phosphate groups at the anomeric center have been displaced by azide togive the glycosyl azides, key intermediates in the synthesis of glycosyl amino acids. Anomerically enriched diphenyl hexopyranosyl phosphate triesters have been prepared from O-alkyl and -acrylated hexopyranoses, using diphenyl chlorophosphate and 4-N,N-dimethylaminopyridine. Glycosyl phosphate triesters of D-gluco-, D-galacto-, D-manno, 2-acetamido-2-deoxy-D-gluco-, L-fuco-, and L-rhamno-pyranosyl derivatives have been obtained by this procedure. At temperatures 0° and above, and under thermodynamic control, diphenyl glycosyl phosphates cis to the pyranosyl C-2 substituent are formed predominantly, whereas at low temperatures and under kinetic control, glycosyl phosphate triesters having 1,2-trans stereochemistry are obtained. The β-glycosyl phosphate triesters of D-glucose and D-galactose derivatives are unstable and undergo anomerization to the α-glycosyl phosphate triesters, in contrast to the stable β-phosphate derivatives of L-rhamnose and D-mannose. These phosphate triesters have been deprotected to glycosyl phosphate triethylammonium salts, suitable for the preparation of other key biological derivatives, such as nucleotide sugars. In addition, the diphenyl phosphate groups at the anomeric center have been displaced by azide to give the glycosyl azides, key intermediates in the synthesis of glycosyl amino acids.
Stereoselective synthesis of L-amino acids via Strecker and Ugi reactions on carbohydrate templates
Kunz,Pfrengle,Ruck,Sager
, p. 1039 - 1042 (2007/10/02)
L-Amino acid derivatives are stereoselectively synthesized in high yield using 2,3,4-tri-O-pivaloyl-α-D-arabinopyranosylamine or 2,3,4-tri-O-pivaloyl-β-L-fucopyranosylamine as the chiral auxiliary in Strecker and Ugi reactions.
