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.
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 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.