108149-60-6Relevant articles and documents
Generating Stereodiversity: Diastereoselective Fluorination and Highly Diastereoselective Epimerization of α-Amino Acid Building Blocks
Wei, Wei,Khangarot, Rama Kanwar,Stahl, Lothar,Veresmortean, Cristina,Pradhan, Padmanava,Yang, Lijia,Zajc, Barbara
, p. 3574 - 3578 (2018)
Diastereoselective fluorination of N-Boc (R)- and (S)-2,2-dimethyl-4-((arylsulfonyl)methyl)oxazolidines and a previously unknown diastereoselective epimerization at the fluorine-bearing carbon atom α to the sulfone was realized. Diastereoselectivities of both reactions were excellent for benzothiazolyl sulfones, allowing access to two enantiomerically pure diastereomers from one chiral precursor. To demonstrate synthetic utility, the benzothiazolyl sulfones were converted to diastereomerically pure (S,S)- and (R,S)-benzyl sulfones via sulfinate salts and to amino acids. To understand the diastereoselectivities, DFT analysis was performed.
Synthesis of D-erythro-sphingosine and D-erythro sphinganine via 3- ketosphinganine
Hoffman, Robert V.,Tao, Junhua
, p. 3953 - 3956 (1998)
D-erythro- sphingosine and D-erythro-sphinganine can be produced in protected form from serine by a synthetic approach in which the normal biological intermediate 3-ketosphinganine in protectyed form, is a key synthetic intermediate. The sequence is short and convergent, proceeds in good overall yields (? 30% for 6 steps) and with excellent stereocontrol (>91% de, >95% ee).
A straightforward synthesis of N-tert-butoxycarbonyl serinate acetonide methyl ester
Branquet,Durand,Vo-Quang,Le Goffic
, p. 153 - 156 (1993)
N-tert-Butoxycarbonyl serinate acetonide methyl ester, an important intermediate in organic synthesis, can be obtained in large quantity according to the procedure described herein.
Ceramides: Branched alkyl chains in the sphingolipid siblings of diacylglycerol improve biological potency
Kang, Ji-Hye,Garg, Himanshu,Sigano, Dina M.,Francella, Nicholas,Blumenthal, Robert,Marquez, Victor E.
, p. 1498 - 1505 (2009)
The synthesis of a small number of ceramide analogues containing a combination of linear and highly branched alkyl chains on either the d-sphingosine or the N-acyl core of the molecule is reported. Regardless of location, the presence of the branched chain improves potency relative to the positive control, C2 ceramide; however, the most potent compound (4) has the branched side chain as part of the d-sphingosine core. The induction of apoptosis by 4 in terms of Annexin V binding and DiOC6 labeling was superior to that achieved with C2 ceramide.
Solution-phase automated synthesis of an α-amino aldehyde as a versatile intermediate
Masui, Hisashi,Yosugi, Sae,Fuse, Shinichiro,Takahashi, Takashi
, p. 106 - 110 (2017)
A solution-phase automated synthesis of the versatile synthetic intermediate, Garner's aldehyde, was demonstrated. tert-Butoxycarbonyl (Boc) protection, acetal formation, and reduction of the ester to the corresponding aldehyde were performed utilizing our originally developed automated synthesizer, ChemKonzert. The developed procedure was also useful for the synthesis of Garner's aldehyde analogues possessing fluorenylmethyloxycarbonyl (Fmoc) or benzyloxycarbonyl (Cbz) protection.
Chemoenzymatic Total Synthesis of GM3 Gangliosides Containing Different Sialic Acid Forms and Various Fatty Acyl Chains
Yu, Hai,Gadi, Madhusudhan Reddy,Bai, Yuanyuan,Zhang, Libo,Li, Lei,Yin, Jun,Wang, Peng G.,Chen, Xi
, p. 8672 - 8682 (2021)
Gangliosides are sialic acid-containing glycosphingolipids that have been found in the cell membranes of all vertebrates. Their important biological functions are contributed by both the glycan and the ceramide lipid components. GM3 is a major ganglioside
Synthesis and application of N-3,5-dinitrobenzoyl and C3 symmetric diastereomeric chiral stationary phases
Yu, Jeong Jae,Ryoo, Jae Jeong
, p. 587 - 596 (2022/01/20)
Three diastereomeric chiral compounds, namely, (R,R)-(+)-2-amino-1,2-diphenylethanol, (1S,2R)-(+)-2-amino-1,2-diphenylethanol, and (1R,2R)-(+)-1,2-diphenylethylenediamine were used as starting materials for preparing three N-3,5-dinitrobenzoyl derivative
In search of small molecules that selectively inhibit mboat4
Ding, Hui,Harran, Patrick G.,Hollibaugh, Ryan A.,Liu, Haixia,Murzinski, Emily S.,Saha, Ishika,Strugatsky, David,Tontonoz, Peter
, (2021/12/24)
Ghrelin is a 28-residue peptide hormone produced by stomach P/D1 cells located in oxyntic glands of the fundus mucosa. Post-translational octanoylation of its Ser-3 residue, catalyzed by MBOAT4 (aka ghrelin O-acyl transferase (GOAT)), is essential for the binding of the hormone to its receptor in target tissues. Physiological roles of acyl ghrelin include the regulation of food intake, growth hormone secretion from the pituitary, and inhibition of insulin secretion from the pancreas. Here, we describe a medicinal chemistry campaign that led to the identification of small lipopeptidomimetics that inhibit GOAT in vitro. These molecules compete directly for substrate binding. We further describe the synthesis of heterocyclic inhibitors that compete at the acyl coenzyme A binding site.
