188656-15-7Relevant articles and documents
Synthesis of α,α-Difluorinated Phosphonate pSer/pThr Mimetics via Rhodium-Catalyzed Asymmetric Hydrogenation of β-Difluorophosphonomethyl α-(Acylamino)acrylates
Chen, Hong-Xue,Kang, Jie,Chang, Rong,Zhang, Yun-Lai,Duan, Hua-Zhen,Li, Yan-Mei,Chen, Yong-Xiang
supporting information, p. 3278 - 3281 (2018/06/11)
A novel and facile synthetic strategy for α,α-difluorinated phosphonate mimetics of phosphoserine/phosphothreonine utilizing rhodium-catalyzed asymmetric hydrogenation was developed. The dehydrogenated substrate β-difluorophosphonomethyl α-(acylamino)acrylates were first prepared from protected serine/threonine followed by asymmetric hydrogenation using the rhodium-DuPhos catalytic system to generate the chiral center(s). These important phosphonate building blocks were successfully incorporated into phosphatase-resistant peptides, which displayed similar inhibition to the 14-3-3 ζ protein as the parent pSer/pThr peptides.
Design and synthesis of prolylcarboxypeptidase (PrCP) inhibitors to validate PrCP as a potential target for obesity
Zhou, Changyou,Garcia-Calvo, Margareta,Pinto, Shirly,Lombardo, Matthew,Feng, Zhe,Bender, Kate,Pryor, Kellyann D.,Bhatt, Urmi R.,Chabin, Renee M.,Geissler, Wayne M.,Shen, Zhu,Tong, Xinchun,Zhang, Zhoupeng,Wong, Kenny K.,Roy, Ranabir Sinha,Chapman, Kevin T.,Yang, Lihu,Xiong, Yusheng
experimental part, p. 7251 - 7263 (2010/12/25)
Prolylcarboxypeptidase (PrCP) is a serine protease that may have a role in metabolism regulation. A class of reversible, potent, and selective PrCP inhibitors was developed starting from a mechanism based design for inhibiting this serine protease. Compound 8o inhibits human and mouse PrCP at IC 50 values of 1 and 2 nM and is not active (IC50 > 25 μM) against a panel of closely related proteases. It has lower serum binding than its close analogues and is bioavailable in mouse. Subchronic dosing of 8o in PrCP-/- and WT mice at 100 mg/kg for 5 days resulted in a 5% reduction in body weight in WT mice and a 1% reduction in PrCP KO mice.
A Versatile Chemo-Enzymatic Route to Enantiomerically Pure β-Branched α-Amino Acids
Roff, Geoffrey J.,Lloyd, Richard C.,Turner, Nicholas J.
, p. 4098 - 4099 (2007/10/03)
A series of diastereoisomers of β-methyl-β-phenylalanine analogues 1a?f have been prepared in enantiomerically pure form using a combination of chemo- and biocatalysis. Starting from l-threonine methyl ester 2, a range of β,β-disubstituted didehydroamino
A Highly Enantioselective Asymmetric Hydrogenation Route to β-(2R,3S)-Methyltryptophan
Hoerrner, R. Scott,Askin, David,Volante, R. P.,Reider, Paul J.
, p. 3455 - 3458 (2007/10/03)
Asymmetric hydrogenation of a protected (Z)-dehydro-β-methyltryptophan derivative 2 with (R,R)-Me-DuPHOS-Rh catalysis was achieved in 97percent ee.Deprotection then afforded (2R,3S)-β-methyltryptophan 1.
A convenient cross-coupling route to α,β,γ,δ-unsaturated amino acids
Burk, Mark J.,Allen, John G.,Kiesman, William F.,Stoffan, Karen M.
, p. 1309 - 1312 (2007/10/03)
β-Bromoenamide esters are coupled stereospecifically to vinylboronic acids via a palladium-catalyzed Suzuki reaction. This cross-coupling proceeds under mild conditions with Pd(OAc)2 in 95% EtOH at 50°C and produces amino acids with 1,3-diene side chains in high yields.
