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Erwinia tasmaniensis levansucrase shows enantiomer selection for (S)-1,2,4-butanetriol.
Polsinelli I, Salomone-Stagni M, Benini S. Polsinelli I, et al. Acta Crystallogr F Struct Biol Commun. 2022 Aug 1;78(Pt 8):289-296. doi: 10.1107/S2053230X2200680X. Epub 2022 Jul 26. Acta Crystallogr F Struct Biol Commun. 2022. PMID: 35924596 Free PMC article.
The structure of Erwinia tasmaniensis levansucrase in complex with (S)-1,2,4-butanetriol and its biochemical characterization suggests the possible application of short aliphatic moieties containing polyols with defined stereocentres in fructosy …
The structure of Erwinia tasmaniensis levansucrase in complex with (S)-1,2,4-butanetriol and its biochemi …
Production of optically active 1,2,4-butanetriol from corresponding racemate by Microbial stereoinversion.
Yamada-Onodera K, Norimoto A, Kawada N, Furuya R, Yamamoto H, Tani Y. Yamada-Onodera K, et al. J Biosci Bioeng. 2007 May;103(5):494-6. doi: 10.1263/jbb.103.494. J Biosci Bioeng. 2007. PMID: 17609168
Sterigmatomyces elviae DSM 70852 produced 12 g/l (S)-1,2,4-butanetriol (enantiomeric excess >99.9%) from 20 g/l racemate in 82 h. From the results of the inversion of an (R)-isomer to an (S)-isomer and GC-MS, it was suggested that (R)- …
Sterigmatomyces elviae DSM 70852 produced 12 g/l (S)-1,2,4-butanetriol (enantiomeric excess >99.9%) fr …
Impact of nature and length of linker incorporated in agonists on toll-like receptor 9-mediated immune responses.
Putta MR, Yu D, Bhagat L, Wang D, Zhu FG, Kandimalla ER. Putta MR, et al. J Med Chem. 2010 May 13;53(9):3730-8. doi: 10.1021/jm100177p. J Med Chem. 2010. PMID: 20361743
In the present study, we have examined the impact of length, nature, and stereochemistry of the linker incorporated in agonists for TLR9 activation. The new linkers studied include (S)-(-)-1,2,4-butanetriol, 1,3,5-pentanetriol, cis,cis- …
In the present study, we have examined the impact of length, nature, and stereochemistry of the linker incorporated in agonists for TLR9 act …
First total synthesis of the pro-resolving lipid mediator 7(S),12(R),13(S)-Resolvin T2 and its 13(R)-epimer.
Rodriguez AR, Spur BW. Rodriguez AR, et al. Tetrahedron Lett. 2020 May 14;61(20):151857. doi: 10.1016/j.tetlet.2020.151857. Epub 2020 Mar 19. Tetrahedron Lett. 2020. PMID: 32863450 Free PMC article.
The first total synthesis of the pro-resolving lipid mediator 7(S),12(R),13(S)-Resolvin T2 [7(S), 12(R), 13(S)-RvT2] and its 13(R)-epimer, derived from n-3 docosapentaenoic acid (n-3 DPA), are described. 7(S), 12(R), 13(S)-RvT2 and its 13 …
The first total synthesis of the pro-resolving lipid mediator 7(S),12(R),13(S)-Resolvin T2 [7(S), 12(R), 13(S)-R …
Total Synthesis of the Antidiabetic (Type 2) Lipid Mediator Protectin DX/PDX.
Sancéau JY, Maltais R, Poirier D, Marette A. Sancéau JY, et al. J Org Chem. 2019 Jan 18;84(2):495-505. doi: 10.1021/acs.joc.8b01973. Epub 2018 Dec 26. J Org Chem. 2019. PMID: 30586310
The first total synthesis of a lipid mediator derived from natural omega-3-fatty acid docosahexaenoic acid (DHA), 10 S,17 S-diHDHA (also referred to as protectin DX/PDX), was achieved in a convergent route (29 steps). The two chiral hydroxyl groups at C-10 and C-17 …
The first total synthesis of a lipid mediator derived from natural omega-3-fatty acid docosahexaenoic acid (DHA), 10 S,17 S-di …
Chiral ligand exchange micellar electrokinetic chromatography using borate anion as a central ion.
Kodama S, Yamamoto A, Iio R, Aizawa S, Nakagomi K, Hayakawa K. Kodama S, et al. Electrophoresis. 2005 Oct;26(20):3884-9. doi: 10.1002/elps.200500327. Electrophoresis. 2005. PMID: 16167312
Three compounds having 1,2-diol structure (1-phenyl-1,2-ethanediol, 3-phenoxy-1,2-propanediol, and 3-benzyloxy-1,2-propanediol) were enantioseparated by ligand exchange MEKC using (5S)-pinanediol (SPD) as a chiral sel …
Three compounds having 1,2-diol structure (1-phenyl-1,2-ethanediol, 3-phenoxy-1,2-propanedi …
Enantioselective total synthesis of (+)-azimine and (+)-carpaine.
Sato T, Aoyagi S, Kibayashi C. Sato T, et al. Org Lett. 2003 Oct 16;5(21):3839-42. doi: 10.1021/ol030088w. Org Lett. 2003. PMID: 14535723
[reaction: see text] The enantioselective total syntheses of (+)-azimine and (+)-carpaine have been developed, starting with (S)-1,2,4-butanetriol as a single source of chirality. The key common feature in these syntheses involves stereoselectiv …
[reaction: see text] The enantioselective total syntheses of (+)-azimine and (+)-carpaine have been developed, starting with (S)-1 …
Total Synthesis of (-)-Cylindricine C.
Molander GA, Rönn M. Molander GA, et al. J Org Chem. 1999 Jul 9;64(14):5183-5187. doi: 10.1021/jo990363l. J Org Chem. 1999. PMID: 34237875
(-)-Cylindricine C has been synthesized from commercially available (S)-(-)-1,2,4-butanetriol in 11 steps with an overall yield of 12%. The key step utilizes a CrCl(2) reduction of an azide to form the corresponding amine with a subsequen …
(-)-Cylindricine C has been synthesized from commercially available (S)-(-)-1,2,4-butanetriol in 11 steps …