212913-84-3

Usage

Uses

Used in Pharmaceutical Industry:
14-Pentadecynoic acid is used as a precursor for the development of bioactive compounds for the treatment of various human diseases, including cancer, inflammation, and infectious diseases. Its anti-inflammatory and neuroprotective properties make it a promising candidate for the development of new therapeutic agents.
Used in Biotechnology Industry:
14-PDA is used as a starting material for the production of valuable bioactive compounds, which can be utilized in various biotechnological applications, such as the development of antifungal agents and other pharmaceuticals.
Used in Materials Science:
14-Pentadecynoic acid is used as a building block for the production of polymer materials due to its unique chemical structure and reactivity. This allows for the creation of innovative materials with specific properties for various applications in the materials science field.

Upstream product

• 56909-04-7 14-Pentadecynoic acid, methyl ester 
• 101434-22-4 ethyl 14-oxotetradecanoate 
• 910631-00-4 (E)-14-Benzyloxy-tetradec-2-enoic acid ethyl ester 
• 134834-32-5 12-(benzyloxy)dodecan-1-ol 
• 910631-01-5 ethyl 14-hydroxytetradecanoate 
• 173074-89-0 12‐(benzyloxy)dodecanal 
• 77113-48-5 (5-chloropent-1-ynyl)trimethylsilane 
• 1262788-53-3 10-oxo-15-trimethylsilanyl-pentadec-14-yonic acid methyl ester 
• 14065-32-8 methyl 10-chloro-10-oxodecanoate 

Downstream Products

• 910630-80-7 C₇₉H₁₁₃NO₁₁Si 
• 910630-95-4 C₇₉H₁₁₃NO₁₁Si 
• 910630-86-3 (17R,18S,19S,20S,21S,22S)-18,19,20,21,22-Pentakis-benzyloxy-25-((S)-1-tert-butoxycarbonyl-2-methyl-propylcarbamoyl)-17-hydroxy-pentacos-14-ynoic acid 
• 910630-96-5 (17R,18S,19S,20S,21S,22S)-18,19,20,21,22-Pentakis-benzyloxy-25-((R)-1-tert-butoxycarbonyl-2-methyl-propylcarbamoyl)-17-hydroxy-pentacos-14-ynoic acid 
• 910630-85-2 C₂₄H₄₆O₂Si 

Relevant academic research and scientific papers

Switching head group selectivity in mammalian sphingolipid biosynthesis by active-site engineering of sphingomyelin synthases

SM is a fundamental component of mammalian cell membranes that contributes to mechanical stability, signaling, and sorting. Its production involves the transfer of phosphocholine from phosphatidylcholine onto ceramide, a reaction catalyzed by SM synthase (SMS) 1 in the Golgi and SMS2 at the plasma membrane. Mammalian cells also synthesize trace amounts of the SM analog ceramide phosphoethanolamine (CPE), but the physiological relevance of CPE production is unclear. Previous work revealed that SMS2 is a bifunctional enzyme producing both SM and CPE, whereas a closely related enzyme, sphingomyelin synthase-related protein (SMSr)/SAMD8, acts as a monofunctional CPE synthase in the endoplasmatic reticulum. Using domain swapping and site-directed mutagenesis on enzymes expressed in defined lipid environments, we here identified structural determinants that mediate head group selectivity of SMS family members. Notably, a single residue adjacent to the catalytic histidine in the third exoplasmic loop profoundly influenced enzyme specificity, with glutamic acid permitting SMS-catalyzed CPE production and aspartic acid confining the enzyme to produce SM. An exchange of exoplasmic residues with SMSr proved sufficient to convert SMS1 into a bulk CPE synthase. This allowed us to establish mammalian cells that produce CPE rather than SM as the principal phosphosphingolipid and provide a model of the molecular interactions that impart catalytic specificity among SMS enzymes.

Stereochemistry of sagittamide A: Prediction and confirmation

The C5-C10 relative stereochemistry of sagittamide A was predicted, with the use of the 3JH,H profiles assembled from the spin-coupling constants reported in the literature. The predicted relative stereochemistry was then confirmed by a total synthesis of two relevant remote diastereomers. The absolute configuration of sagittamide A was established through a detailed 1H NMR analysis of the two remote diastereomers, followed by doping experiments of them with the authentic natural product.