25488-25-9Relevant academic research and scientific papers
Stereoselective synthesis of β-alkylated α-amino acids via palladium-catalyzed alkylation of unactivated methylene C(sp3)-H Bonds with Primary Alkyl Halides
Zhang, Shu-Yu,Li, Qiong,He, Gang,Nack, William A.,Chen, Gong
, p. 12135 - 12141 (2013/09/02)
We report a new set of reactions based on the Pd-catalyzed alkylation of methylene C(sp3)-H bonds of aliphatic quinolyl carboxamides with α-haloacetate and methyl iodide and applications in the stereoselective synthesis of various β-alkylated α-amino acids. These reactions represent the first generally applicable method for the catalytic alkylation of unconstrained and unactivated methylene C-H bonds with high synthetic relevance. When applied with simple isotope-enriched reagents, they also provide a convenient and powerful means to site-selectively incorporate isotopes into the carbon scaffolds of amino acid compounds.
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.
An efficient and stereodivergent synthesis of threo- and erythro-β-methylphenylalanine. Resolution of each racemic pair by semipreparative HPLC
Alías, Miriam,López, María Pilar,Cativiela, Carlos
, p. 885 - 891 (2007/10/03)
threo and erythro diastereoisomers of the constrained amino acid (βMe)Phe can be obtained separately on a multigram scale through a three-step synthesis from the corresponding Z and E isomers of 2-phenyl-4(α-phenylethylidene)-5(4H)-oxazolone. The 5(4H)-ox
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
Catalytic asymmetric hydrogenation of α-(acetamido)acrylates using TRAP trans-chelating chiral bisphosphine ligands: Remarkable effects of ligand P-substituent and hydrogen pressure on enantioselectivity
Kuwano,Sawamura,Ito
, p. 2571 - 2578 (2007/10/03)
The catalytic asymmetric hydrogenation of α-(acetamido)acrylates was carded out with the rhodium complexes prepared from [Rh(cod)2]BF4 and trans-chelating chiral bisphosphine ligands, (S,S)-2,2'-bis[(R)-1-(dialkylphosphino)ethyl]-1,1
SB-203207 and SB-203208, two novel isoleucyl tRNA synthetase inhibitors from a Streptomyces sp. I. Fermentation, isolation and properties
Stefanska, Anna L.,Cassels, Robert,Ready, Sarah J.,Warr, Stephen R.
, p. 357 - 363 (2007/10/03)
Two novel inhibitors of isoleucyl tRNA synthetase designated SB-203207 and SB-203208 have been detected in the culture of a new Streptomyces species. The fermentation, isolation and some properties of the inhibitors are described.
Aza-Darzens asymmetric synthesis of N-(p-toluenesulfinyl)aziridine 2- carboxylate esters from sulfinimines (N-sulfinyl imines)
Davis, Franklin A.,Liu, Hu,Zhou, Ping,Fang, Tianan,Reddy, G. Venkat,Zhang, Yulian
, p. 7559 - 7567 (2007/10/03)
The one-step aza-Darzens reaction of sulfinimines 2 with lithium α- bromoenolates readily affords diversely substituted cis and trans N- sulfinylaziridine 2-carboxylate esters 3 and 7 in good yield and excellent diastereoselectivity. Higher yields, but lower de's, result when a mixture of the α-bromo ester and 2 are treated with base. The N-sulfinyl group is transformed, nearly quantitatively, without ring opening, into the N-tosyl activating group by oxidation with m-CPBA. Selective removal of the N- sulfinyl group in aziridines 3a and 3h with TFA/H2O affords 1H-aziridines 21 which are difficult to prepared by other means. However, C(3) activated azirines such as 3b undergo ring-opening under these conditions. Alternatively, the N-sulfinyl group, even in C(3)-activated aziridines, was selectively and efficiently removed by treatment of the aziridine with 2 equiv of MeMgBr.
A new strategy for the synthesis of four individual isomers of β-methylphenylalanine
Lung,Li,Lou,Hruby
, p. 57 - 61 (2007/10/02)
The application of an allylic strain effect in boron enolates and asymmetric Michael-like addition/electrophilic bromination reactions is reported for the asymmetric synthesis of the individual isomers of unusual constrained amino acids. For β-substituted
Exploration for Large-scale Stereoselective Synthesis of Unusual Amino Acids by using 4-Phenyoxazolidin-2-one as a New Chiral Resolution Reagent
Li, Guigen,Patel, Dinesh,Hruby, Victor J.
, p. 3057 - 3060 (2007/10/02)
Individual isomers of β-branched α-amino acids have been stereoselectively and asymmetrically synthesized in high yield by a new method which uses 4-phenyloxazolidin-2-one as a novel chiral resolution reagent acting simultaneously as the auxiliary.
