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.
Total Synthesis of the Post-translationally Modified Polyazole Peptide Antibiotic Goadsporin
Dexter, Hannah L.,Williams, Huw E. L.,Lewis, William,Moody, Christopher J.
, p. 3069 - 3073 (2017)
The structurally unique polyazole antibiotic goadsporin contains six heteroaromatic oxazole and thiazole rings integrated into a linear array of amino acids that also contains two dehydroalanine residues. An efficient total synthesis of goadsporin is repo
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 Allyl Amines from α-Amino Acids without Racemization
Moriwake, Toshio,Hamano, Shin-ichi,Saito, Seiki,Torii, Sigeru
, p. 2085 - 2088 (1987)
An extremely simple and practical synthesis of allyl amine derivatives from α-amino acids has been developed involving aldehyde olefination pathway with AlMe3-Zn-CH2I2 reagent which has proven to be crucial for preservation of stereochemical integrity.
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.
Mild and facile procedure for clay-catalyzed acetonide protection and deprotection of N(Boc)-amino alcohols and protection of 1,2-diols
Shaikh, Nadim S.,Bhor, Santosh S.,Gajare, Anil S.,Deshpande, Vishnu H.,Wakharkar, Radhika D.
, p. 5395 - 5398 (2004)
The application of clay as a catalyst for acetonide protection of N(Boc)-amino alcohols and 1,2-diols to obtain good to excellent yields of the acetonide derivatives is described. Acetonide deprotection to obtain the parent amino alcohol was carried out using a similar catalyst in the presence of methanol as solvent. The reaction takes place at room temperature within 2h to give the parent amino alcohol in quantitative yield keeping the N(Boc) group intact.
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.
Synthesis of Nontoxic Fluorous Sphingolipids as Molecular Probes of Exogenous Metabolic Studies for Rapid Enrichment by Fluorous Solid Phase Extraction
Saito, Shota,Murai, Yuta,Usuki, Seigo,Yoshida, Masafumi,Hammam, Mostafa A. S.,Mitsutake, Susumu,Yuyama, Kohei,Igarashi, Yasuyuki,Monde, Kenji
, p. 1045 - 1051 (2017)
Fluorous solid-phase extraction (FSPE) is a useful technique for efficient selective enrichment of fluorous compounds from nonfluorous molecules. Sphingolipids and their metabolites, which are ubiquitous building blocks of eukaryotic and prokaryotic cell membranes, play crucial roles, for example, as signaling molecules. However, details of the functions and metabolic mechanisms of exogenous sphingolipids have remained unknown compared with those of their endogenous analogs. To better understand these unknown roles, chemical probes with appropriate biological and physicochemical properties are needed. In this study, we designed and synthesized new fluorous sphingolipids to reveal these roles. Furthermore, we confirmed that they could be efficiently and rapidly separated from normal sphingolipids by FSPE, and that they hardly showed any cytotoxic activity, similarly to normal sphingolipids at the same dose. We also showed that these fluorinated ceramides could act as metabolic substrates for sphingomyelin synthase 2 (SMS2). This demonstrates their potential for further biological studies.
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.
Alcohol functionality in the fatty acid backbone of sphingomyelin guides the inhibition of blood coagulation
Mallik,Prasad,Das,Sen
, p. 3390 - 3398 (2021)
Cell-surface sphingomyelin (SM) inhibits binary and ternary complex activity of blood coagulation by an unknown mechanism. Here we show the OH functionality of SM contributes in forming the close assembly through intermolecular H-bond and through Ca2+ chelation, which restricts the protein-lipid/protein-protein interactions and thus inhibits the coagulation procedure.
