120686-16-0Relevant articles and documents
N-allyl-N-tert-butyldimethylsilylamine for chiral ligand-controlled asymmetric conjugate addition to tert-butyl alkenoates
Doi, Hirohisa,Sakai, Takeo,Yamada, Ken-Ichi,Tomioka, Kiyoshi
, p. 1850 - 1851 (2004)
The chiral ligand controlled asymmetric conjugate addition reaction of lithium N-allyl-N-(tert-butyldimethylsilyl)amide to alkenoates proceeded smoothly to give, after protodesilylation, the corresponding 3-allylaminoalkanoates with high enantioselectivit
An Asymmetric Ammonia Synthon for Michael Additions
Hawkins, Joel M.,Lewis, Timothy A.
, p. 2114 - 2121 (1992)
The highly diastereoselective 1,4-addition of lithiated chiral amine 1 to α,β-unsaturated esters, followed by hydrogenolysis of the benzylic-type C-N bonds of the 1,4-adducts, provides an asymmetric ammonia synthon for Michael additions.Under optimized co
The kinetic resolution of oxazinones by alcoholysis: access to orthogonally protected β-amino acids
Cronin, Sarah A.,Connon, Stephen J.
supporting information, p. 7348 - 7352 (2021/09/07)
The catalytic, alcoholytic kinetic resolution of oxazinones is reported. A novel, stereochemically dense cinchona alkaloid-based catalyst can facilitate the highly enantiodiscriminatory (Sup to 101) ring-opening of oxazinones equipped with electrophilic aryl units to generate orthogonally protected β-amino acids for the first time.
Controlling Intramolecular Interactions in the Design of Selective, High-Affinity Ligands for the CREBBP Bromodomain
Brand, Michael,Clayton, James,Moroglu, Mustafa,Schiedel, Matthias,Picaud, Sarah,Bluck, Joseph P.,Skwarska, Anna,Bolland, Hannah,Chan, Anthony K. N.,Laurin, Corentine M. C.,Scorah, Amy R.,See, Larissa,Rooney, Timothy P. C.,Andrews, Katrina H.,Fedorov, Oleg,Perell, Gabriella,Kalra, Prakriti,Vinh, Kayla B.,Cortopassi, Wilian A.,Heitel, Pascal,Christensen, Kirsten E.,Cooper, Richard I.,Paton, Robert S.,Pomerantz, William C. K.,Biggin, Philip C.,Hammond, Ester M.,Filippakopoulos, Panagis,Conway, Stuart J.
, p. 10102 - 10123 (2021/07/31)
CREBBP (CBP/KAT3A) and its paralogue EP300 (KAT3B) are lysine acetyltransferases (KATs) that are essential for human development. They each comprise 10 domains through which they interact with >400 proteins, making them important transcriptional co-activa
Acylation of β-Amino Esters and Hydrolysis of β-Amido Esters: Candida antarctica Lipase A as a Chemoselective Deprotection Catalyst
M?enp??, Harri,Kanerva, Liisa T.,Liljeblad, Arto
, p. 1226 - 1232 (2016/04/05)
N-Acylation by lipase A from Candida antarctica (CAL-A) in ethyl butanoate was applied to the kinetic resolution of tert-butyl esters of 3-amino-3-phenylpropanoic acid (E>100), 3-amino-4-methylpentanoic acid (E>100) and 3-aminobutanoic acid (E=60) on 1.0-2.0 m scale. With the N-acylated resolution products, the exceptional ability of CAL-A to hydrolyse amides and bulky tert-butyl esters was then studied. In all N-acylated tert-butyl esters, chemoselectivity favoured the amide bond cleavage. The tert-butyl ester bond was left intact with 3-amino-3-phenylpropanoate, whereas with 3-amino-4-methylpentanoate and 3-aminobutanoate the CAL-A-catalysed hydrolysis of tert-butyl ester followed the amide hydrolysis.
Double asymmetric induction as a mechanistic probe: The doubly diastereoselective conjugate addition of enantiopure lithium amides to enantiopure α,β-unsaturated esters and enantiopure α,β-unsaturated hydroxamates
Davies, Stephen G.,Lee, James A.,Roberts, Paul M.,Thomson, James E.,Yin, Jingda
, p. 6382 - 6403 (2011/09/19)
The doubly diastereoselective conjugate addition of the antipodes of lithium N-benzyl-N-(α-methylbenzyl)amide to a range of enantiopure α,β-unsaturated esters [derived from Corey's 8-phenylmenthol chiral auxiliary] and enantiopure α,β-unsaturated hydroxamates [derived from our 'chiral Weinreb amide' auxiliary (S)-N-1-(1′-naphthyl)ethyl-O-tert- butylhydroxylamine] has been used as a mechanistic probe to determine the reactive conformations of these acceptors.
Burkholderia cepacia lipase and activated β-lactams in β-dipeptide and β-amino amide synthesis
Li, Xiang-Guo,Laehitie, Maria,Kanerva, Liisa T.
, p. 1857 - 1861 (2008/12/21)
The work describes fluorine-activated and N-Boc-activated β-lactams as acyl donors to N-nucleophiles in the presence of Burkholderia cepacia lipase (lipase PS-D). Fluorine activation at the β-lactam ring causes the ring to open in high enantioselectivity
Parallel synthesis of homochiral β-amino acids
Davies, Stephen G.,Mulvaney, Andrew W.,Russell, Angela J.,Smith, Andrew D.
, p. 1554 - 1566 (2008/02/09)
The parallel asymmetric synthesis of an array of 30 β-amino acids of high enantiomeric purity using the conjugate addition of homochiral lithium N-benzyl-N-(α-methylbenzyl)amide as the key step is accomplished. The experimental simplicity and highly practical nature of the protocol is demonstrated by the efficient parallel conversion of 15 α,β-unsaturated esters to both enantiomeric series of the corresponding β-amino acids in high overall yields and selectivities with minimal purification involved in each step of the reaction protocol.
New kelatorphan-related inhibitors of enkephalin metabolism: Improved antinociceptive properties
Xie,Soleilhac,Schmidt,Peyroux,Roques,Fournie-Zaluski
, p. 1497 - 1503 (2007/10/02)
In order to improve the in vivo protection of enkephalins from enzymatic degradation, a new series of inhibitors derived from kelatorphan [HONHCOCH2CH(CH2Ph)CONHCH(CH3)COOH], the first-described complete inhibitor of enkephalin metabolism, were designed by modification of the C-terminal amino acid. The progressive lengthening of the chain of this residue shows that a β-alanine seems to be the best basic model for the conception of such types of compounds. On the other hand, the methylation of the amide bond, which is well accepted by aminopeptidase N (EC 3.4.11.2) and dipeptidylaminopeptidase, induced a significant loss of affinity for neutral endopeptidase -24.11. Starting from these data, compounds containing a variously substituted β-alanine residue and corresponding to the general formula HONHCOCH2CH(CH2Ph)CONHCH(R1)CH(R2)COOH were synthesized. All these molecules inhibit neutral endopeptidase -24.11 and dipeptidylaminopeptidase in the nanomolar range, and those containing an aromatic chain (compound 7A, R1 = CH2Ph,R2 = H, and compound 8A, R1 = Ph, R2 = H) inhibit the biologically relevant aminopeptidase N, with IC50's around 10-8 M. Intracerebroventricular injection in mice of these multienzyme inhibitors produced an efficient and naloxone-reversible analgesic response (hot plate test): compounds 7A and 8A were shown to be more potent than kelatorpohan in increasing the jump latency time, in agreement with their in vitro properties, and these new compounds were found to increase the forepaw lick latency, a reflex considered as a typical morphine response.
