71015-20-8Relevant academic research and scientific papers
PHYTOSPHINGOSINE DERIVATIVES AS ADJUVANTS IN IMMUNE STIMULATION
-
Page/Page column 50-51, (2022/01/04)
The invention relates to phytosphingosine derivatives, suitable as adjuvants in immune stimulation. The invention further relates to pharmaceutical compositions comprising such compounds and the medical use of said compounds and/or compositions in therapeutic or prophylactic methods of immune stimulation in a subject, and for use in the treatment of a disease, for which stimulation of an immune response in a subject produces a therapeutic benefit. The invention further relates to the phytosphingosine derivative as described herein for use as an adjuvant in a method of vaccinating a subject. The invention further relates to the phytosphingosine derivative as described herein for use in stimulating antibody production, stimulating an immune response against infection, stimulating an immune response against a cancer, or preventing and/or treating septic shock. The invention further relates to a method for the manufacture of said derivatives comprising an Ugi-4-component reaction (Ugi-4CR).
Influence of the C-terminal substituent on the crystal-state conformation of Adm peptides
Mir, Fatemeh M.,Crisma, Marco,Toniolo, Claudio,Lubell, William D.
, (2020/03/11)
The bis-functionalized diamondoid α-amino acid 2-aminoadamantane-2-carboxylic acid (Adm) has been used as the building block of four Nα-formyl homo-dipeptide alkylamide sequences via a solution-phase Ugi multicomponent reaction approach. The conformers of these peptides have been determined in the crystalline state by X-ray diffraction to distinguish the influences of the C-terminal substituent. One of the Adm peptides folds into an open and a hydrogen-bonded γ-turn geometry. Moreover, 3D-structures have been observed featuring two consecutive γ-turns in an incipient γ-helical structure, a significantly distorted nonhelical β-turn, as well as an S-shaped conformation with opposite helical screw senses. A significant topological variety is thus exhibited by the -Adm-Adm- sequences contingent on their C-terminal substituents, illustrating both the broad conformational potential and the need for further characterization of this sterically bulky residue in explorations of its ?, ψ space.
Iodide-Catalyzed Synthesis of Secondary Thiocarbamates from Isocyanides and Thiosulfonates
Mampuys, Pieter,Zhu, Yanping,Sergeyev, Sergey,Ruijter, Eelco,Orru, Romano V. A.,Van Doorslaer, Sabine,Maes, Bert U. W.
supporting information, p. 2808 - 2811 (2016/07/06)
A new method for the synthesis of secondary thiocarbamates from readily available isocyanides and thiosulfonates with broad functional group tolerance is reported. The reaction proceeds under mild reaction conditions in isopropanol and is catalyzed by inexpensive sodium iodide.
Isoselenocyanates derived from amino acid esters: An expedient synthesis and application to the assembly of selenoureidopeptidomimetics, unsymmetrical Selenoureas and selenohydantoins
Hemantha, Hosahalli P.,Sureshbabu, Vommina V.
, p. 644 - 651 (2011/09/14)
An important class of organoselenium compounds-α-isoselenocyanato esters 4 hasbeen prepared by a reaction of α-isocyano esters with elemental selenium powder. The reaction issimple, rapid and all the isoselenocyanates havebeen isolated as stable ones after chromatographic purification. These hitherto unreported classes of molecules would be useful building blocks for the preparation of variety of selenium containing peptidomimetics. In this study, the utility of the title molecules in the preparation of selenoureidopeptidomimetics 6, unsymmetrical selenoureas 8 and selenohydantoins 10 isdemonstrated.
Ammonium chloride promoted three-component synthesis of 5-iminooxazoline and its subsequent transformation to macrocyclodepsipeptide
Pirali, Tracey,Tron, Gian Cesare,Masson, Geraldine,Zhu, Jieping
, p. 5275 - 5278 (2008/09/18)
(Chemical Equation Presented) A three-component reaction of an α,α-disubstituted α-isocyanoacetamide, an aldehyde and an amino alcohol afforded the 5-iminooxazoline, which, upon saponification, cyclized under acidic conditions to provide the macrocyclodepsipeptide in good overall yield.
Synthesis of tripeptides containing α,α-diphenylglycine by the modified Ugi reaction
Yamada, Takashi,Omote, Yuichiro,Yamanaka, Yoshinori,Miyazawa, Toshifumi,Kuwata, Shigeru
, p. 991 - 998 (2007/10/03)
The modified Ugi reaction has been developed to synthesize tripeptides containing α,α-diphenylglycine (Dph) together with bulky amino acids. By the use of diphenylmethanimine, N-benzyloxycarbonyl (Z) amino acids and isocyanides derived from amino acids, very crowded tripeptides such as Z- Aib-Dph-Aib-OMe, Z-Ac6c-Dph-Aib-OMe, Z-Dph-Dph-Dph-OMe, etc. have been synthesized.
