The asymmetric alkylation reaction of glycine derivatives catalyzed by the novel chiral phase transfer catalysts

Wang, Ziyu; Huang, Daorui; Xu, Pei; Dong, Xiaoyang; Wang, Xiaolong; Dai, Zhenya

doi:10.1016/j.tetlet.2015.01.063

Cited by 10 publications

(3 citation statements)

References 13 publications

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“…However, these synthetic routes depend on toxic reagents such as methylsulfonyl chloride. 37,38 To minimize the effect of toxic reagents, 1-ethyl-3-(3-dimethyl aminopropyl) carbodiimide/4-dimethylaminopyridine (EDCI/DMAP) as a coupling agent, a chiral intermediate i.e. derivative of glycine non-proline 27 was synthesized starting with proline and then alkylating in the presence of sodium tert-butoxide which obtained 28 (Fig.…”

Section: Chemical Synthesismentioning

confidence: 99%

Reprogramming natural proteins using unnatural amino acids

et al. 2021

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Section: Chemical Synthesismentioning

confidence: 99%

Reprogramming natural proteins using unnatural amino acids

et al. 2021

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“…Despite the growing diversity and range of applications of ncAAs, their synthesis is still a challenge [ 11 , 12 , 13 ]. The traditional chemical synthesis methods are limited by harsh reaction conditions [ 14 ], highly volatile toxic substances [ 15 , 16 ], environmental pollution and high raw material costs [ 17 ]. Metabolic engineering is an emerging technique that could potentially solve these issues and enable the green and efficient production of ncAAs.…”

Section: Introductionmentioning

confidence: 99%

Advances in Biosynthesis of Non-Canonical Amino Acids (ncAAs) and the Methods of ncAAs Incorporation into Proteins

Chen,

Xin,

Zhang

et al. 2023

Molecules

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The functional pool of canonical amino acids (cAAs) has been enriched through the emergence of non-canonical amino acids (ncAAs). NcAAs play a crucial role in the production of various pharmaceuticals. The biosynthesis of ncAAs has emerged as an alternative to traditional chemical synthesis due to its environmental friendliness and high efficiency. The breakthrough genetic code expansion (GCE) technique developed in recent years has allowed the incorporation of ncAAs into target proteins, giving them special functions and biological activities. The biosynthesis of ncAAs and their incorporation into target proteins within a single microbe has become an enticing application of such molecules. Based on that, in this study, we first review the biosynthesis methods for ncAAs and analyze the difficulties related to biosynthesis. We then summarize the GCE methods and analyze their advantages and disadvantages. Further, we review the application progress of ncAAs and anticipate the challenges and future development directions of ncAAs.

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“… , One of such products, β-isocupreidine (β-ICD) is a long recognized catalyst particularly effective in the Baylis–Hillman reaction . There are no convincing reports of derivatives incorporating quinuclidine nitrogen atom in the extension of the ring system. Thus, we propose unique derivatives of Cinchona alkaloids by extending aza-bicyclo[2.2.2]octane cage to a tricyclic system with central quaternary nitrogen atom.…”

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confidence: 99%

Tricyclic Quaternary Ammonium Salts Derived from Cinchona Alkaloids

et al. 2016

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Tricyclic systems with quaternary bridgehead nitrogen atoms are rare but an interesting class of compounds. Chiral quinuclidine derivative salts with fused five and six-membered rings (X-ray) were obtained via modification of Cinchona alkaloids. The ease of ring formation was dependent on its size, while even mild activation sufficed to close the five membered ring. On the other hand the systems with fused benzene and a six-membered ring formed atropisomers separated by a barrier of ca. 15 kcal/mol, whose interconversion was studied by DFT and NMR.

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The asymmetric alkylation reaction of glycine derivatives catalyzed by the novel chiral phase transfer catalysts

Cited by 10 publications

References 13 publications

Reprogramming natural proteins using unnatural amino acids

Reprogramming natural proteins using unnatural amino acids

Advances in Biosynthesis of Non-Canonical Amino Acids (ncAAs) and the Methods of ncAAs Incorporation into Proteins

Tricyclic Quaternary Ammonium Salts Derived from Cinchona Alkaloids

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