67799-92-2Relevant academic research and scientific papers
Chiral beta-amino acid derivative and preparation method thereof
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Paragraph 0076-0080, (2018/03/28)
The invention discloses a chiral beta-amino acid derivative and a preparation method thereof. The structural formula of the chiral beta-amino acid derivative is represented by a formula I (shown in the description). The preparation method comprises the steps of mixing a mixture of a carbonyl compound and N,O-acetal with chiral primary-tertiary diamine organic small-molecule catalyst, strong acid and weak acid to react, so as to obtain the chiral beta-amino acid derivative, wherein the carbonyl compound includes aldehyde and/or ketone. The chiral beta-amino acid derivative is catalyzed by virtue of the chiral primary-tertiary diamine organic small-molecule catalyst with a simple structure, is synthesized through a one-step method, and is solvent-free, simple and efficient.
Catalytic Asymmetric Mannich Reaction with N-Carbamoyl Imine Surrogates of Formaldehyde and Glyoxylate
You, Yang'en,Zhang, Long,Cui, Linfeng,Mi, Xueling,Luo, Sanzhong
supporting information, p. 13814 - 13818 (2017/10/09)
N,O-acetals (NOAcs) were developed as bench stable surrogates for N-carbamoyl, (Boc, Cbz and Fmoc) formaldehyde and glyoxylate imines in asymmetric Mannich reactions. The NOAcs can be directly utilized in the chiral primary amine catalyzed Mannich reactions of both acyclic and cyclic β-ketocarbonyls with high yields and excellent stereoselectivity. The current reaction offers a straightforward approach in the asymmetric synthesis of α- or β-amino carbonyls bearing chiral quaternary centers in a practical and highly stereocontrolled manner.
Additivity or cooperativity: Which model can predict the influence of simultaneous incorporation of two or more functionalities in a ligand molecule?
Nasief, Nader N.,Hangauer, David
, p. 897 - 915 (2015/05/27)
Predicting how binding affinity responds to ligand structural modifications in structure-activity relationship studies (SAR) is a major challenge in medicinal chemistry. This is particularly true when two or more of these modifications are carried out simultaneously. In this study, we present binding affinity data from several series of thermolysin inhibitors in which simultaneous structural modifications were investigated to determine whether they are cooperative or additive. Data revealed that, while additivity is at work in some cases, cooperativity is more commonly demonstrated. Cooperativity and additivity were then correlated with ligand descriptors, such as the spacing and the topological features of the modified groups, in a manner that may provide guidance as to when each model should be utilized. Cooperativity was particularly associated with contiguous groups and small unbranched hydrophobic side chain. Additivity, on the other hand, was associated with moderately distant hydrophobic group combinations and side chain branching. Such correlations can improve the predictability of SAR studies and can provide a starting point for additional investigations that may lead to further significant enhancements in the current scoring functions.
Influence of neighboring groups on the thermodynamics of hydrophobic binding: An added complex facet to the hydrophobic effect
Nasief, Nader N.,Hangauer, David
, p. 2315 - 2333 (2014/04/17)
The thermodynamic consequences of systematic modifications in a ligand side chain that binds in a shallow hydrophobic pocket, in the presence and absence of a neighboring ligand carboxylate group, were evaluated using isothermal titration calorimetry (ITC
Synthesis of vicinal aminoalcohols by stereoselective aza-wacker cyclizations: Access to (-)-acosamine by redox relay
Weinstein, Adam B.,Schuman, David P.,Tan, Zhi Xu,Stahl, Shannon S.
supporting information, p. 11867 - 11870 (2013/11/19)
Diastereoselective aza-Wacker cyclization of O-allyl hemiaminals under aerobic conditions enables efficient access to 1,2-aminoalcohol derivatives from allylic alcohols. The scope of this method is presented and its utility is highlighted in a streamlined
Water mediated ligand functional group cooperativity: The contribution of a methyl group to binding affinity is enhanced by a COO- group through changes in the structure and thermodynamics of the hydration waters of ligand-thermolysin complexes
Nasief, Nader N.,Tan, Hongwei,Kong, Jing,Hangauer, David
, p. 8283 - 8302 (2013/01/15)
Ligand functional groups can modulate the contributions of one another to the ligand-protein binding thermodynamics, producing either positive or negative cooperativity. Data presented for four thermolysin phosphonamidate inhibitors demonstrate that the d
Convergent asymmetric route to produce a key intermediate towards the synthesis of a garft inhibitor
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Page 13-14, (2010/02/10)
The invention relates to processes for the preparation of a key intermediate in the synthesis of a GARFT inhibitor of formula (Ia) containing a 4-methyl-substituted thiophene core: wherein said key intermediate has the following formula (I): wherein each
STEREOSELECTIVE SYNTHESIS OF γ-HYDROXY-α-AMINO ACIDS via INTRAMOLECULAR AMIDOMERCURATION
Harding, Kenn E.,Marman, Thomas H.,Nam, Do-hyun
, p. 5605 - 5614 (2007/10/02)
A general method for the stereoselective conversion of homoallylic alcohols to erythro- or threo-γ-hydroxy-α-amino acids is described.The key step is the stereoselective mercuric ion-initiated cyclofunctionalization of acylaminomethyl ether derivatives of
Peptide Sweeteners. 3. Effect of Modifying the Peptide Bond on the Sweet Taste of L-Aspartyl-L-phenylalanine Methyl Ester and Its Analogues
MacDonald, Scott A.,Willson, C. Grant,Chorev, Michael,Vernacchia, Fred S.,Goodman, Murray
, p. 413 - 420 (2007/10/02)
A series of analogues designed to assess the importance of the amide bond in the dipeptide sweetener L-aspartyl-L-phenylalanine methyl ester has been synthesized and tested.The peptide bond was methylated, replaced by an ester bond, or reversed.All of the
