58645-35-5Relevant academic research and scientific papers
Substrate analogs for the investigation of deoxyxylulose 5-phosphate reductoisomerase inhibition: Synthesis and evaluation
Phaosiri, Chanokporn,Proteau, Philip J.
, p. 5309 - 5312 (2004)
Deoxyxylulose 5-phosphate (DXP) analogs were synthesized and evaluated as alternative substrates and inhibitors of recombinant Synechocystis PCC6803 DXP reductoisomerase (DXR; EC 1.1.1.267). Five of the compounds tested (1,2-dideoxy-d-threo-3-hexulose 6-phosphate, 1-deoxy-l-ribulose 5-phosphate, 2S,3R-dihydroxybutyramide 4-phosphate, 4S-hydroxypentan-2-one 5-phosphate, and 3S-hydroxypentan-2-one 5-phosphate) acted as relatively weak competitive inhibitors when compared to fosmidomycin. A sixth compound, 3R,4S-dihydroxy-5- oxohexylphosphonic acid, served as an alternate substrate, as has recently been reported for the same compound with Escherichia coli DXR.
Total Synthesis of Tiacumicin B: Implementing Hydrogen Bond Directed Acceptor Delivery for Highly Selective β-Glycosylations
Beau, Jean-Marie,Fran?ois-Eude, Marc,Genta-Jouve, Grégory,Jeanne-Julien, Louis,Masson, Guillaume,Norsikian, Stéphanie,Roulland, Emmanuel,Servajean, Vincent,Tresse, Cedric
supporting information, p. 6612 - 6616 (2020/03/03)
A total synthesis of tiacumicin B, a natural macrolide whose remarkable antibiotic properties are used to treat severe intestinal infections, is reported. The strategy is in part based on the prior synthesis of the tiacumicin B aglycone, and on the decisive use of sulfoxides as anomeric leaving groups in hydrogen-bond-mediated aglycone delivery (HAD). This new HAD variant permitted highly β-selective rhamnosylation and noviosylation. To increase convergence, the rhamnosylated C1–C3 fragment thus obtained was anchored to the C4–C19 aglycone fragment by adapting the Suzuki–Miyaura cross-coupling used for the aglycone synthesis. Ring-size-selective macrolactonization provided a compound engaged directly in the noviolysation step with virtually total β selectivity. The final efficient removal of all the protecting groups provided synthetic tiacumicin B.
Intercepted dehomologation of aldoses by N-heterocyclic carbene catalysis-a novel transformation in carbohydrate chemistry
Draskovits, Markus,Kalaus, Hubert,Stanetty, Christian,Mihovilovic, Marko D.
, p. 12144 - 12147 (2019/10/21)
The development of an N-heterocyclic carbene (NHC) catalysed intercepted dehomologation of aldoses is reported. The unique selectivity of NHCs for aldehydes is exploited in the complex context of reducing sugars. Examples of strong substrate governance for either intercepted dehomologation or a subsequent redox-lactonisation were identified and mechanistically understood. More importantly, it was shown that catalyst design allowed the tuning of the selectivity of the reaction with structurally unbiased starting materials towards either of the two scenarios.
Synthesis of a novel C-branched polyhydroxylated cyclic nitrone
Wu, Qing-Kun,Li, Yi-Xian,Jia, Yue-Mei,Yu, Chu-Yi
supporting information, p. 909 - 912 (2017/05/16)
A novel C-branched polyhydroxylated cyclic nitrone 25, which could be a valuable intermediate for the synthesis of C-branched pyrrolidine iminosugars, was synthesized starting from the commercially available L-arabinose in 29.0% total yield.
Partially Acetylated or Benzoylated Arabinose Derivatives as Structurally Simple Organogelators: Effect of the Ester Protecting Group on Gel Properties
Rajkamal,Pathak, Navendu P.,Halder, Tanmoy,Dhara, Shubhajit,Yadav, Somnath
, p. 11323 - 11329 (2017/08/26)
Sugar-based low-molecular-weight gelators (LMWGs) have been used for various applications for a long time. Herein, structurally simple, ester-protected arabinosides are reported as low-molecular-weight organogelators (LMOGs) that are able to gel aromatic solvents, as well as petrol and diesel. Studies on the mechanical strength of the gels, through detailed rheological experiments, indicate that gels from the 1,2-dibenzoylated arabinose gelator possess better mechanical properties than those from the 1,2-diacetylated gelator. These results are interpreted in terms of the tendency of the former to form fibers with comparatively lower diameter than those of the latter, based on detailed field-emission SEM and AFM studies. Investigations of the interactions responsible for the self-assembly of gelators through IR spectroscopy and wide-angle X-ray scattering reveal that the primary interactions responsible are hydrogen bonds between the hydroxyl groups and ester C=O, which is absent in the solid state of the gelators. In addition, π interactions present in the 1,2-dibenzoylated derivative result in a more regular arrangement, which, in turn, leads to better mechanical properties of the gels compared with those of the 1,2-diacetylated gelator.
BIOTIN ALTERANT, STREPTAVIDIN MUTANT, AND USES THEREOF
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Paragraph 0053; 0054, (2016/01/25)
It is an object of the present invention to provide a mutant streptavidin with a reduced affinity for natural biotin, and also to provide a modified biotin having a high affinity for the mutant streptavidin with a reduced affinity for natural biotin. Acco
Design and synthesis of biotin analogues reversibly binding with streptavidin
Yamamoto, Tomohiro,Aoki, Kiyoshi,Sugiyama, Akira,Doi, Hirofumi,Kodama, Tatsuhiko,Shimizu, Yohei,Kanai, Motomu
supporting information, p. 1071 - 1078 (2015/03/31)
Two new biotin analogues, biotin carbonate 5 and biotin carbamate 6, have been synthesized. These molecules were designed to reversibly bind with streptavidin by replacing the hydrogen-bond donor NH group(s) of biotin's cyclic urea moiety with oxygen. Biotin carbonate 5 was synthesized from L-arabinose (7), which furnishes the desired stereochemistry at the 3,4-cis-dihydroxy groups, in 11% overall yield (over 10 steps). Synthesis of biotin carbamate 6 was accomplished from L-cysteine-derived chiral aldehyde 33 in 11% overall yield (over 7 steps). Surface plasmon resonance analysis of water-soluble biotin carbonate analogue 46 and biotin carbamate analogue 47 revealed that KD values of these compounds for binding to streptavidin were 6.7×10-6M and 1.7×10-10M, respectively. These values were remarkably greater than that of biotin (KD=10-15M), and thus indicate the importance of the nitrogen atoms for the strong binding between biotin and streptavidin.
Syntheses of arabinose-derived pyrrolidine catalysts and their applications in intramolecular Diels-Alder reactions
Shing, Tony K. M.,Wu, Kwun W.,Wu, Ho T.,Xiao, Qicai
, p. 1754 - 1762 (2015/02/19)
Six chiral hydroxylated pyrrolidine catalysts were synthesized from commercially available D-arabinose in seven steps. Various aromatic substituents α to the amine can be introduced readily by a Grignard reaction, which enables facile optimization of the catalyst performance. The stereoselectivities of these catalysts have been assessed by comparing with those of MacMillan's imidazolidinone in a known intramolecular Diels-Alder (IMDA) reaction of a triene. Two additional IMDA reactions of symmetrical dienals with concomitant desymmetrisation further established the potential use of these novel amine catalysts. These pyrrolidines are valuable catalysts for other synthetic transformations.
Total syntheses of cochliomycin B and zeaenol
Gao, Yangguang,Liu, Jun,Wang, Linlin,Xiao, Ming,Du, Yuguo
, p. 2092 - 2098 (2014/04/17)
Divergent syntheses of two 14-membered resorcylic acid lactones (RALs), cochliomycin B (6) and zeaenol (22), have been accomplished. The key feature in our strategy was the facile construction of three contiguous stereogenic centers in the title molecules
Enantiomeric organogelators from d-/l-arabinose for phase selective gelation of crude oil and their gel as a photochemical micro-reactor
Rajkamal,Chatterjee, Debnath,Paul, Abhijit,Banerjee, Srirupa,Yadav, Somnath
supporting information, p. 12131 - 12134 (2015/02/19)
Enantiomeric d- or l-arabinose based low molecular-weight organogelators (LMOGs), accessible in a single synthetic step from d-/l-arabinose have been found to be efficient gelators for aromatic solvents and refined and crude oil. The organogel has also been successfully used as a micro-reactor for a photochemical reaction. This journal is
