A Concise Synthesis of <scp>L</scp>‐Pyrrolysine

Han, Man‐Yi; Wang, Huaizhen; An, Wan‐Kai; Jia, Ju‐Ying; Ma, Baochun; Zhang, Yuan; Wang, Wei

doi:10.1002/chem.201300403

Cited by 15 publications

(6 citation statements)

References 40 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The above results suggest that addition of an MF template can regulate the pore structure of the catalyst with enlarged micropores and formation of mesoporous structures, which could be beneficial to improve the stability and activity of the catalyst. Fe−N−C HPCs also showed an abundant mesopore size distri‐bution, but the proportion of micropores decreased significantly (Figure 2b), which may result in decreased active sites and thus of declined catalyst activity [28] . The specific surface areas, micropore areas and external areas of the prepared catalysts are listed in Table 1.…”

Section: Resultsmentioning

confidence: 99%

“…This may be due to the fact that using a SiO 2 template may bring a large number of mesopores and macropores formation on the outer structure and increase of their exposure; meanwhile, it may also lead to decreasing of the proportion of micropores that will reduce the density of active sites and eventually to impair the catalytic activity. On the other hand, MF may generate CO 2 during the pyrolysis process, which erodes the outer carbon structure and brings more micropores to anchor the iron atoms; and at the same time, the release of ammonia introduces more N atoms into the outer carbon structure (Table S1), which is beneficial to the promotion of the catalyst activity [28] …”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Three‐Dimensional Hierarchical Porous Fe, N‐Doped Hollow Carbon Nanospheres as Stable Electrocatalyst for Efficient Oxygen Reduction Reaction in Both Acidic and Alkaline Electrolytes

Sun

Guo

et al. 2022

ChemistrySelect

View full text Add to dashboard Cite

3D hierarchical porous Fe, N‐doped hollow carbon nano‐spheres (Fe−N−C HPNCs) as efficient ORR electrocatalyst were obtained using melamine‐formaldehyde resin (MF) nanospheres as thermal sacrificial hard template to optimize the pore structure and provide nitrogen source to the catalyst. The optimized Fe−N−C HPNCs catalyst exhibited excellent catalytic activity with onset (Eonset) and half‐wave (E1/2) potential (Eonset=1.07 V; E1/2=0.90 V vs. RHE) superior to commercial Pt/C catalyst in 0.1 M KOH solution, and demonstrated excellent stability. When applied as cathode electro‐catalyst in a Zn‐air battery, it produced maximum power density (Pmax) of 127 mW cm−2, which is higher than that of commercial Pt/C (Pmax=119 mW cm−2). It also showed good activity (Eonset=0.89 V; E1/2=0.78 V) in 0.1 M HClO4 electrolyte with significantly enhanced stability (ΔE1/2=−7 mV) relative to the Pt/C catalyst (ΔE1/2=−27 mV).

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Three‐Dimensional Hierarchical Porous Fe, N‐Doped Hollow Carbon Nanospheres as Stable Electrocatalyst for Efficient Oxygen Reduction Reaction in Both Acidic and Alkaline Electrolytes

Sun

Guo

et al. 2022

ChemistrySelect

View full text Add to dashboard Cite

show abstract

“…Supplying cells with an exogenous source of synthetically produced Pyl provides an alternative solution 12 . However, organic synthesis of Pyl is known for its difficulty [12][13][14] and thus remains commercially unavailable.…”

Section: Graphical Abstract Figurementioning

confidence: 99%

Improved pyrrolysine biosynthesis through continuous directed evolution of the complete pathway

Ho¹,

Miller²,

Mattia³

et al. 2020

Preprint

View full text Add to dashboard Cite

Pyrrolysine (Pyl, O) exists in nature as the 22nd proteinogenic amino acid. Despite being a fundamental building block of proteins, studies of Pyl have been hindered by the difficulty and inefficiency of both its chemical and biological syntheses. Here, we improved Pyl biosynthesis via rational engineering and directed evolution of the entire biosynthetic pathway. To accommodate toxicity of Pyl biosynthetic genes in Escherichia coli, we devised an approach termed Alternating Phage Assisted Non-Continuous Evolution (Alt-PANCE) that alternates mutagenic and selective phage growths. The evolved pathway exhibited a 32-fold improved yield of Pyl-containing super- folder green fluorescent protein (sfGFP) compared to the rationally engineered ancestor, whereas the WT pathway produced no detectable quantities of Pyl-containing sfGFP. This study demonstrates that Alt-PANCE provides a general approach for evolving proteins exhibiting toxic side effects, and further provides an improved pathway capable of producing substantially greater quantities of Pyl- proteins in E. coli.

show abstract

“…In the chemical laboratory, only a few synthetic approaches for the preparation of 84 have been developed, and these often suffer from low yields over multistep protocols. , In 2013, Wang et al developed a concise synthesis, which was inspired by their previous work on the enantioselective synthesis of trans -3-substituted prolines. , The key step of their synthesis included an organocatalytic asymmetric Michael addition of nitroalkane 85 to α,β-unsaturated aldehyde 77 for the construction of the C-4 stereogenic center of the pyrroline ring (Scheme ).…”

Section: Iminium-ion Activationmentioning

confidence: 99%

Prevalence of Diarylprolinol Silyl Ethers as Catalysts in Total Synthesis and Patents

et al. 2019

View full text Add to dashboard Cite

Diarylprolinol silyl ethers are among the most utilized stereoselective organocatalysts for the construction of complex molecules. With their debut in 2005, these catalysts have been applied in numerous method developments primarily leveraging enamine and iminium-ion catalysis. These strategies have extended into the preparation of complex molecules in both academic and industrial settings. This Review intends to give an overview of the application of the diarylprolinol silyl ether catalysts in total synthesis. Furthermore, integration of these catalysts in patent literature is also disclosed highlighting the versatility of the catalytic system.

show abstract

A Concise Synthesis of L‐Pyrrolysine

Abstract: Organocatalysis: A concise synthesis of L-pyrrolysine has been accomplished in six steps from simple starting materials. The facile synthetic strategy relies on an organocatalytic Michael addition, an efficient amide coupling, and a challenging method for the imine-bond construction.

Cited by 15 publications

References 40 publications

Three‐Dimensional Hierarchical Porous Fe, N‐Doped Hollow Carbon Nanospheres as Stable Electrocatalyst for Efficient Oxygen Reduction Reaction in Both Acidic and Alkaline Electrolytes

Three‐Dimensional Hierarchical Porous Fe, N‐Doped Hollow Carbon Nanospheres as Stable Electrocatalyst for Efficient Oxygen Reduction Reaction in Both Acidic and Alkaline Electrolytes

Improved pyrrolysine biosynthesis through continuous directed evolution of the complete pathway

Prevalence of Diarylprolinol Silyl Ethers as Catalysts in Total Synthesis and Patents

Contact Info

Product

Resources

About