554-62-1Relevant academic research and scientific papers
Isolation and structure of a new ceramide from the basidiomycete Hygrophorus eburnesus
Qu, Yan,Zhang, Hong-Bin,Liu, Ji-Kai
, p. 241 - 244 (2004)
A new ceramide, named hygrophamide (1), was isolated from the fruiting bodies of the basidiomycetes Hygrophorus eburnesus Fr.. The structure of the compound was elucidated as (2S, 3S, 4R, 2′R)-2-(2′-hydroxy- 9′Z-ene-tetracosanoylamino)-octadecane- 1,3,4-triol (1) by spectral and chemical methods.
Phytoceramides and acylated phytosterol glucosides from Pterospermum acerifolium Willd. seed coat and their osteogenic activity
Dixit, Preety,Chand, Kailash,Khan, Mohd Parvez,Siddiqui, Jawed Akhtar,Tewari, Deepshikha,Ngueguim, Florence Tsofack,Chattopadhyay, Naibedya,Maurya, Rakesh
, p. 117 - 125 (2012)
Phytochemical investigation of seed coats of Pterospermum acerifolium afforded two phytoceramides (1, 2) and two acylated phytosterol glucosides (3, 4) together with five known compounds (5-9). Their structures were elucidated on the basis of extensive sp
Paxillamide: A novel phytosphingosine derivative from the fruiting bodies of Paxillus panuoides
Gao, Jin-Ming,Zhang, An-Ling,Zhang, Cun-Li,Liu, Ji-Kai
, p. 1483 - 1487 (2004)
The new phytosphingosine-type ceramide 1, named paxillamide (=2,3-dihydroxy-N-[(1S,2S,3R)-2,3-dihydroxy-1-(hydroxymethyl)heptadecyl] tetracosanamide), was isolated from the CHCl3/MeOH extract of the fruiting bodies of the Basidiomycete Paxillus panuoides, and its structure was elucidated by spectroscopic and chemical methods.
Convergent evolution of bacterial ceramide synthesis
Ashley, Ben,Campopiano, Dominic J.,Chamberlain, Joshua D.,Coleman, Aimiyah,D’Emilia, Rachel,Fu, Larina,Guan, Ziqiang,Hansen, Matthew E. B.,Klein, Eric A.,Mohan, Eric C.,Nguyen, Hung,Stankeviciute, Gabriele,Tang, Peijun
, (2022/01/06)
The bacterial domain produces numerous types of sphingolipids with various physiological functions. In the human microbiome, commensal and pathogenic bacteria use these lipids to modulate the host inflammatory system. Despite their growing importance, their biosynthetic pathway remains undefined since several key eukaryotic ceramide synthesis enzymes have no bacterial homolog. Here we used genomic and biochemical approaches to identify six proteins comprising the complete pathway for bacterial ceramide synthesis. Bioinformatic analyses revealed the widespread potential for bacterial ceramide synthesis leading to our discovery of a Gram-positive species that produces ceramides. Biochemical evidence demonstrated that the bacterial pathway operates in a different order from that in eukaryotes. Furthermore, phylogenetic analyses support the hypothesis that the bacterial and eukaryotic ceramide pathways evolved independently. [Figure not available: see fulltext.]
Development of an Amino Acid/Hydroxy Oxime Dual Catalyst System for Highly Stereoselective Direct Asymmetric Aldol Reactions in the Presence of Water
Mridha, Moniruzzaman,Ma, Guangning,Palo-Nieto, Carlos,Afewerki, Samson,Cordova, Armando
, p. 383 - 390 (2016/12/24)
An eco-friendly dual catalyst system for stereoselective aldol reactions in the presence of water is described. It is based on the cooperative action of acyclic amino acids and H-bond donating hydroxy oxime catalysts. The synthetic utility of this dual catalyst system was further demonstrated by applying it as the key step in the expeditious and highly stereoselective total synthesis of d-lyxo-phytosphingosine (29% overall yield). Here the amino acid/hydroxy oxime system significantly accelerated the direct aldol reactions in the presence of water as compared to organic solvents. The stereo- and chemoselectivity were also significantly increased.
Divergent total synthesis of D-ribo-phytosphingosine and L-ribo-phytosphingosine from D-ribose
Chun, Jong Soo,Hong, Seung Min,Jeon, Tae Hong,Park, Sook Jin,Son, Han Pyo,Jung, Jun Min,Choi, Young Jae,Kim, In Su,Jung, Young Hoon
, p. 8550 - 8556 (2016/12/09)
Divergent total synthesis of D-ribo-phytosphingosine (1) and L-ribo-phytosphingosine (2) was achieved from readily available D-ribose via cross-metathesis reaction, Wittig reaction, and diastereoselective amination reaction of allylic ethers using chlorosulfonyl isocyanate (CSI) as the key steps. As results, reactions of anti-1,2-dibenzyl ethers 11 and 16 with chlorosulfonyl isocyanate afforded exclusively anti-1,2-amino alcohols 12 and 17 with diastereoselectivity of 32:1 and 31:1 in 75% and 76% yields, respectively. These results could be explained by the neighboring group effect, leading to retention of stereochemistry.
Chemo- and Diastereoselective N-Heterocyclic Carbene-Catalyzed Cross-Benzoin Reactions Using N-Boc-α-amino Aldehydes
Haghshenas, Pouyan,Gravel, Michel
supporting information, p. 4518 - 4521 (2016/09/28)
N-Boc-α-amino aldehydes are shown to be excellent partners in cross-benzoin reactions with aliphatic or heteroaromatic aldehydes. The chemoselectivity of the reaction and the facial selectivity on the amino aldehyde allow cross-benzoin products to be obtained in good yields and good diastereomeric ratios. The developed method is utilized as the key step in a concise total synthesis of d-arabino-phytosphingosine.
Protein and peptide-free synthetic vaccines against streptococcus pneumoniae type 3
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Paragraph 0099, (2015/03/31)
The present invention provides a protein- and peptide-free conjugate comprising a synthetic carbohydrate and a carrier molecule, wherein the synthetic carbohydrate is a Streptococcus pneumoniae type 3 capsular polysaccharide related carbohydrate and the carrier molecule is a glycosphingolipid. Said conjugate and pharmaceutical composition thereof are useful for immunization against diseases associated with Streptococcus pneumoniae, and more specifically against diseases associated with Streptococcus pneumoniae type 3.
PROTEIN AND PEPTIDE-FREE SYNTHETIC VACCINES AGAINST STREPTOCOCCUS PNEUMONIAE TYPE 3
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Page/Page column 71; 72, (2015/04/15)
The present invention provides a protein- and peptide-free conjugate comprising a synthetic carbohydrate and a carrier molecule, wherein the synthetic carbohydrate is a Streptococcus pneumoniae type 3 capsular polysaccharide related carbohydrate and the carrier molecule is a glycosphingolipid. Said conjugate and pharmaceutical composition thereof are useful for immunization against diseases associated with Streptococcus pneumoniae, and more specifically against diseases associated with Streptococcus pneumoniae type 3.
CARBOHYDRATE-GLYCOLIPID CONJUGATE VACCINES
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Paragraph 0235, (2015/09/28)
The present invention relates to the field of synthesizing and biologically evaluating of a novel class of carbohydrate-based vaccines. The new vaccines consist of a multi-modular structure which allows applying the vaccine to a whole variety of pathogenes. This method allows preparing vaccines against all pathogens expressing immunogenic carbohydrate antigens. As conjugation of antigenic carbohydrates to proteins is not required the conjugate vaccine is particularly heat stable. No refrigeration is required, a major drawback of protein-based vaccines.
