109786-77-8Relevant academic research and scientific papers
The Chiral Target of Daptomycin Is the 2R,2′S Stereoisomer of Phosphatidylglycerol
Moreira, Ryan,Taylor, Scott D.
, (2021/12/09)
Daptomycin (dap) is an important antibiotic that interacts with the bacterial membrane lipid phosphatidylglycerol (PG) in a calcium-dependent manner. The enantiomer of dap (ent-dap) was synthesized and was found to be 85-fold less active than dap against
DRUG CONTAINING TARGETING LIPOSOMES
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Page/Page column 9, (2021/03/05)
Described herein are novel, modified targeting peptides which can be incorporated within liposomes. Additionally, described herein are liposomes containing the modified targeting peptides. Liposomes preferably comprise a lipid-based bilayer and at least o
CANNABINOID CONTAINING TARGETING LIPOSOMES
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Page/Page column 9-10, (2021/03/05)
Described herein are liposomes containing modified targeting peptides. Liposomes preferably comprise a lipid-based bilayer and at least one cannabinoid. Also provided herein are methods for making the liposomes, and methods for treatment of diseases of th
Stereospecific synthesis of phosphatidylglycerol using a cyanoethyl phosphoramidite precursor
Storch, Judith,Struzik, Zachary J.,Thompson, David H.,Weerts, Ashley N.
, (2020/07/03)
Phosphatidylglycerols (PG) are a family of naturally occurring phospholipids that are responsible for critical operations within cells. PG are characterized by an (R) configuration in the diacyl glycerol backbone and an (S) configuration in the phosphoglycerol head group. Herein, we report a synthetic route to provide control over the PG stereocenters as well as control of the acyl chain identity.
Substrate specificity of tuliposide-converting enzyme, a unique non-ester-hydrolyzing carboxylesterase in tulip: Effects of the alcohol moiety of substrate on the enzyme activity
Kato, Yasuo,Futanaga, Takashi,Nomura, Taiji
supporting information, p. 664 - 667 (2019/01/04)
6-Tuliposides A (PosA) and B (PosB) are glucose esters accumulated in tulip (Tulipa gesneriana) as major defensive secondary metabolites. Pos-converting enzymes (TgTCEs), which we discovered previously from tulip, catalyze the conversion reactions of PosA
Enzyme-mediated enantioselective hydrolysis of 1,2-diol monotosylate derivatives bearing an unsaturated substituent
Matsumoto,Oohana,Hashimoto,Usuda,Shimoda,Ohshima,Suzuki,Togawa
supporting information, p. 3981 - 3988 (2018/06/15)
We have succeeded in the easy preparation of optically active 1,2-diol monotosylates bearing an unsaturated substituent via enzymatic hydrolysis. Lipase PS quickly catalyzes the hydrolyses of 2-acetoxybut-3-enyl tosylate, which has a double bond, and 2-acetoxybut-3-ynyl tosylate, which has a triple bond, with excellent enantioselectivity to afford the corresponding optically active compounds. The reaction is also applicable to acetates with a longer chain, which has a double bond at the terminus. To demonstrate the applicability of this method, enantiomerically pure (R)-massoialactone, a natural coconut flavor, has been synthesized from racemic 2-acetoxypent-4-enyl tosylate in several steps. Furthermore, the enzyme can recognize the stereochemistry of olefins, and the (Z)-alkenyl structure is more suitable for the enantioselective hydrolysis than the (E)-isomer.
Employing BINOL-Phosphoroselenoyl Chloride for Selective Inositol Phosphorylation and Synthesis of Glycosyl Inositol Phospholipid from Entamoeba histolytica
Aiba, Toshihiko,Suehara, Sae,Choy, Siew-Ling,Maekawa, Yuuki,Lotter, Hannelore,Murai, Toshiaki,Inuki, Shinsuke,Fukase, Koichi,Fujimoto, Yukari
, p. 8304 - 8308 (2017/06/23)
The chemical synthesis of glycosyl inositol phospholipids from Entamoeba histolytica is reported. The key feature of this synthesis is a regioselective phosphorylation reaction that occurs through desymmetrization of a myo-inositol derivative with phosphoroselenoyl chloride. A new protecting-group strategy was developed that utilizes allyl and alloc groups to synthesize complex glycolipids bearing unsaturated lipids. These developments provided an efficient synthetic route for various complex inositol phospholipids and their analogues. Furthermore, the binding affinity of the synthetic inositol phospholipids with mouse CD1d molecules has been evaluated, as well as the immunostimulatory activity.
PSEUDO-CYCLIC LIPID COMPOUND
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Paragraph 0097; 0098, (2016/10/07)
PROBLEM TO BE SOLVED: To provide a novel glycerol ester compound or glycerol ether compound that can be synthesized relatively easily, and a molecular aggregate comprising them. SOLUTION: This invention provides a novel pseudo-cyclic lipid compound in which glycerol two molecules bond to univalent and divalent alcohol or carboxylic acid through ether or ester linkage, in which a fluorine atom or a non-terminal triple bond or both of them is introduced in the molecule. COPYRIGHT: (C)2016,JPOandINPIT
Stereoselective synthesis of the head group of archaeal phospholipid PGP-Me to investigate bacteriorhodopsin-lipid interactions
Cui, Jin,Kawatake, Satoshi,Umegawa, Yuichi,Lethu, Sbastien,Yamagami, Masaki,Matsuoka, Shigeru,Sato, Fuminori,Matsumori, Nobuaki,Murata, Michio
supporting information, p. 10279 - 10284 (2015/10/28)
Phosphatidylglycerophosphate methyl ester (PGP-Me), a major constituent of the archaeal purple membrane, is essential for the proper proton-pump activity of bacteriorhodopsin (bR). We carried out the first synthesis of the bisphosphate head group of PGP-M
Next generation macrocyclic and acyclic cationic lipids for gene transfer: Synthesis and in vitro evaluation
Jubeli, Emile,Maginty, Amanda B.,Abdul Khalique, Nada,Raju, Liji,Abdulhai, Mohamad,Nicholson, David G.,Larsen, Helge,Pungente, Michael D.,Goldring, William P.D.
supporting information, p. 6364 - 6378 (2015/10/05)
Previously we reported the synthesis and in vitro evaluation of four novel, short-chain cationic lipid gene delivery vectors, characterized by acyclic or macrocyclic hydrophobic regions composed of, or derived from, two 7-carbon chains. Herein we describe
