205495-51-8Relevant academic research and scientific papers
Novel peptides comprising furanoid sugar amino acids for the treatment of cancer
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, (2010/02/10)
Anticancer peptides which incorporate furanoid sugar amino acids and compositions made using these peptides are described. Methods for synthesis of the peptides and for preparing the furanoid sugar amino acids are disclosed. The peptides and compositions made using the peptides have pharmacological applications of these peptides especially in the treatment and prevention of cancer and tumors.
Conformational studies of 3,4-dideoxy furanoid sugar amino acid containing analogs of the receptor binding inhibitor of vasoactive intestinal peptide
Chakraborty, Tushar K.,Ramakrishna Reddy,Sudhakar,Uday Kumar,Jagadeshwar Reddy,Kiran Kumar,Kunwar, Ajit C.,Mathur, Archna,Sharma, Rajan,Gupta, Neena,Prasad, Sudhanand
, p. 8329 - 8339 (2007/10/03)
Conformational analysis of vasoactive intestinal peptide (VIP) receptor binding inhibitor Leu1-Met2-Tyr3-Pro 4-Thr5-Tyr6-Leu7-Lys8 1 by various NMR techniques and constrained molecular dynamics (MD) simulation studies revealed that the molecule had a turn structure involving its Tyr 3-Pro4-Thr5-Tyr6 moiety with intramolecular hydrogen bond between Tyr6NH→Tyr3CO. In order to mimic the structure of 1, peptidomimetic analogs 2-4 were synthesized using conformationally constrained scaffolds of 3,4-dideoxy furanoid sugar amino acids (2S,5R)-ddSaa1 5 and its enantiomer (2R,5S)-ddSaa2 6. All these analogs displayed well defined three-dimensional structures akin to that found in 1. Peptides 2 and 3, which differed only in the sugar amino acid stereochemistry, show propensity of structures with identical intramolecular hydrogen bonds between ThrNH→MetCO. A similar structure with a hydrogen bond between TyrNH→MetCO was observed in 4. Graphical Abstract.
An enantioselective ring expansion route leading to furanose and pyranose nucleosides featuring spirodiketopiperazines at the anomeric position
Paquette, Leo A.,Brand, Stephen,Behrens, Carsten
, p. 2010 - 2025 (2007/10/03)
A study directed at the enantioselective synthesis of spirodiketopiperazine homologues of hydantocidin is described. Furanoid glycals, systems that are amenable to C-5 metalation in the presence of tert- butyllithium, are readily coupled to N-protected 2,3-azetidinediones provided that at least 1 equiv of BF3·OEt2 is present to curb enolization. The resulting 1:1 mixtures of carbinols undergo smooth ring expansion to spirocyclic keto amides when heated with pyridinium p-toluenesulfonate in benzene. 1,2-Acyl shifts operate exclusively. Since attempts to engage these products in Beckmann rearrangement proved singularly unsuccessful, recourse was alternatively made to new methodology based upon sequential Baeyer- Villiger oxidation and ammonolysis. The data show that the first of these steps occurs with exclusive migration of the quaternary carbon. Furthermore, nucleophilic attack by NH3 can be directed regioselectively to the anomeric region. If heating is supplied during acid-promoted cyclization to the spirodiketopiperazines, spiropyranose derivatives are produced in a complementary process. The central issue of this synthesis effort was the utilization of 4-phenylseleno-substituted furanoid glycals so as to ultimately enable introduction of the cis-diol functionality at C-3 and C-4 (hydantocidin numbering).
A ring-expansion route to analogues of dideoxyhydantocidin
Paquette, Leo A.,Behrens, Garsten
, p. 31 - 35 (2007/10/03)
The acid-catalyzed rearrangement of hydroxy β-lactam (12), formed by addition of the enantiopure dihydrofuranyllithium (10a) to N-benzyl-2,3-azetidinedione, has been investigated as a potential route to spirocyclic nucleosides.
