85719-40-0Relevant articles and documents
Enzymatic Polymerization of an Ibuprofen-Containing Monomer and Subsequent Drug Release
Stebbins, Nicholas D.,Yu, Weiling,Uhrich, Kathryn E.
, p. 1115 - 1124 (2015)
Novel ibuprofen-containing monomers comprising naturally occurring and biocompatible compounds were synthesized and subsequently polymerized via enzymatic methods. Through the use of a malic acid sugar backbone, ibuprofen was attached as a pendant group,
Selective Monoacylation of Diols and Asymmetric Desymmetrization of Dialkyl meso-Tartrates Using 2-Pyridyl Esters as Acylating Agents and Metal Carboxylates as Catalysts
Hashimoto, Yuki,Michimuko, Chiaki,Yamaguchi, Koki,Nakajima, Makoto,Sugiura, Masaharu
supporting information, p. 9313 - 9321 (2019/08/12)
With 2-pyridyl benzoates as acylating agents and Zn(OAc)2 as a catalyst, 1,2-diols, 1,3-diols, and catechol were selectively monoacylated. Furthermore, the highly enantioselective desymmetrization of meso-tartrates was achieved for the first time, utilizing 2-pyridyl esters and NiBr2/AgOPiv/Ph-BOX in CH3CN or CuCl2/AgOPiv/Ph-BOX in EtOAc catalyst systems (up to 96% ee). The latter catalyst system was also effective for the kinetic resolution of dibenzyl dl-tartrate.
Peniphenone and Penilactone Formation in Penicillium crustosum via 1,4-Michael Additions of ortho-Quinone Methide from Hydroxyclavatol to γ-Butyrolactones from Crustosic Acid
Fan, Jie,Liao, Ge,Kindinger, Florian,Ludwig-Radtke, Lena,Yin, Wen-Bing,Li, Shu-Ming
supporting information, p. 4225 - 4229 (2019/03/19)
Penilactones A and B consist of a γ-butyrolactone and two clavatol moieties. We identified two separate gene clusters for the biosynthesis of these key building blocks in Penicillium crustosum. Gene deletion, feeding experiments, and biochemical investiga
Synthesis of orthogonally protected (2S)-2-amino-adipic acid (α-AAA) and (2S,4 R)-2-amino-4-hydroxyadipic acid (Ahad)
Yadav, Saroj,Taylor, Carol M.
, p. 5401 - 5409 (2013/07/26)
(2S,4R)-2-Amino-4-hydroxyadipic acid (Ahad) building block 45 was synthesized in 11 steps and 6.5% overall yield from commercially available materials. Key steps in stereocontrol were an asymmetric conjugate addition employing a proline-based catalyst and a syn-selective intramolecular-conjugate addition of an oxygen nucleophile to an α,β-unsaturated ester. To enable incorporation of α-amino-adipic acid (α-AAA) and Ahad into peptides, a truly orthogonal protecting group scheme was developed, encompassing an allyloxycarbonyl (Alloc) carbamate for Nα, a tert-butyl ester for the δ-COOH, an acetol ester for the α-COOH, and a tert- butyldimethylsilyl ether for the γ-hydroxy group of Ahad.
Straightforward total synthesis of 2-O-feruloyl-L-malate, 2-O-sinapoyl-L-malate and 2-O-5-hydroxyferuloyl-L-malate
Allais, Florent,Martinet, Sophie,Ducrot, Paul-Henri
scheme or table, p. 3571 - 3578 (2010/03/02)
A synthetic method for the preparation of 2-O-feruloylL-malic acid, 2-O-sinapoyl-L-malic acid and 2-O-5-hydroxyferuloyl-L-malic acid from malic acid and ferulic, sinapic, and hydroxyferulic acids, respectively, using Steglich esterification is described.
Stereospecific high-affinity TRPV1 antagonists: Chiral N-(2-benzyl-3- pivaloyloxypropyl) 2-[4-(methylsulfonylamino)phenyl]propionamide analogues
Ryu, Hyungchul,Jin, Mi-Kyoung,Su, Yeon Kim,Choi, Hyun-Kyung,Kang, Sang-Uk,Dong, Wook Kang,Lee, Jeewoo,Pearce, Larry V.,Pavlyukovets, Vladimir A.,Morgan, Matthew A.,Tran, Richard,Toth, Attila,Lundberg, Daniel J.,Blumberg, Peter M.
, p. 57 - 67 (2008/09/18)
Previously, we reported the thiourea antagonists 2a and 2b as potent and high affinity TRPV1 antagonists. For further optimization of the lead compounds, a series of their amide and α-substituted amide surrogates were investigated and novel chiral N-(2-be
(2R,3S)- and (2S,3R)-2-benzyl-3,4-epoxybutanoic acid as highly efficient and fast acting pseudomechanism-based inactivators for carboxypeptidase A: design, asymmetric synthesis and inhibitory kinetics
Lee, Soo Suk,Li, Zhi-Hong,Lee, Dong Ha,Kim, Dong H.
, p. 2877 - 2882 (2007/10/02)
2-benzyl-3,4-epoxybutanoic acid (BEBA) was studied as an irreversible inhibitor for the zinc-containing protease, carboxypeptidase A.Of four possible stereoisomers, those having a 2R,3S- and a 2S,3R- configuration inhibited carboxypeptidase A in a time-de
A new, short and efficient synthesis of both enantiomers of carnitine
Bellamy,Bondoux,Dodey
, p. 7323 - 7326 (2007/10/02)
A short, efficient and enantioselective synthesis of both (R) and (S) enantiomers of carnitine is reported starting with (R) or (S) malic acid and involving a chemoselective reduction step.