Synthesis of Guanidines and Some of Their Biological Applications

Shaw, Julian; Grayson, David H.; Rozas, Isabel

doi:10.1007/7081_2015_174

Cited by 12 publications

(8 citation statements)

References 130 publications

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“…All the intermediates in the CAPA pathway, i.e., agmatine, CAPA, and APA, bear the guanidine group that can form hydrogen bonds and cation-π interaction with the pathway enzymes. This ability of the guanidine group, which is widely exploited in synthetic medicinal chemistry (46,47), may contribute to the high affinity of CAPADH and CAPADC toward their substrates.…”

Section: Discussionmentioning

confidence: 99%

A bacterial spermidine biosynthetic pathway via carboxyaminopropylagmatine

Xi,

Nie,

Gao

et al. 2023

Sci. Adv.

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Spermidine, a ubiquitous polyamine, is known to be required for critical physiological functions in bacteria. Two principal pathways are known for spermidine biosynthesis, both of which involve aminopropylation of putrescine. Here, we identified a spermidine biosynthetic pathway via a previously unknown metabolite, carboxyaminopropylagmatine (CAPA), in a model cyanobacterium Synechocystis sp. PCC 6803 through an approach combining 13 C and 15 N tracers, metabolomics, and genetic and biochemical characterization. The CAPA pathway starts with reductive condensation of agmatine and l -aspartate-β-semialdehyde into CAPA by a previously unknown CAPA dehydrogenase, followed by decarboxylation of CAPA to form aminopropylagmatine, and ends with conversion of aminopropylagmatine to spermidine by an aminopropylagmatine ureohydrolase. Thus, the pathway does not involve putrescine and depends on l -aspartate-β-semialdehyde as the aminopropyl group donor. Genomic, biochemical, and metagenomic analyses showed that the CAPA-pathway genes are widespread in 15 different phyla of bacteria distributed in marine, freshwater, and other ecosystems.

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Section: Discussionmentioning

confidence: 99%

A bacterial spermidine biosynthetic pathway via carboxyaminopropylagmatine

Xi,

Nie,

Gao

et al. 2023

Sci. Adv.

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“…O emprego destes tiófilos, como agente de dessulfurização formam intermediários carbodiimidas eletrofílicas que, por sua vez, é rapidamente atacada quando na presença de uma amina nucleofílica 13. 12,18 1 Essa metodologia é extremamente robusta e sinteticamente útil. Por exemplo, a reação de uma variedade de aminas aromáticas e alifáticas com N, N-bis--terc-butoxi-carboniltioureia 14 na presença de Et 3 N e HgCl 2 em CH 2 Cl 2 (Esquema 3) produz as correspondentes guanidinas 15 protegidas com excelentes rendimentos (78-92%).…”

Section: Síntese De Guanidinasunclassified

Química Orgânica: Conceitos, Fundamentos e Avanços

2024

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Esta obra constituiu-se a partir de um processo colaborativo entre professores, estudantes e pesquisadores que se destacaram e qualificaram as discussões neste espaço formativo. Resulta, também, de movimentos interinstitucionais e de ações de incentivo à pesquisa que congregam pesquisadores das mais diversas áreas do conhecimento e de diferentes Instituições de Educação Superior públicas e privadas de abrangência nacional e internacional. Tem como objetivo integrar ações interinstitucionais nacionais e internacionais com redes de pesquisa que tenham a finalidade de fomentar a formação continuada dos profissionais da educação, por meio da produção e socialização de conhecimentos das diversas áreas do Saberes. Agradecemos aos autores pelo empenho, disponibilidade e dedicação para o desenvolvimento e conclusão dessa obra. Esperamos também que esta obra sirva de instrumento didático-pedagógico para estudantes, professores dos diversos níveis de ensino em seus trabalhos e demais interessados pela temática.

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“…While pyridinium and imidazolium lipids are more biocompatible compared to quaternary ammonium lipids due to the heterocyclic ring head groups, [ 61 ] guanidine has a p K a value of ≈ 13.6 and exists exclusively as guanidinium in neutral water with a highly stable charge due to efficient resonance stabilization of the charge and solvation by water molecules. [ 62 ] As a result, they can effectively package the nucleic acid while delocalizing the positive charge. On the other hand, ionizable lipids that exhibit pH‐sensitive charge density in the head group were proposed to further enhance the biocompatibility of the cationic lipids and even improve the RNA delivery efficiency.…”

Section: Lnp As a Versatile Platform For Rna Encapsulation And Deliverymentioning

confidence: 99%

High‐Precision Synthesis of RNA‐Loaded Lipid Nanoparticles for Biomedical Applications

Seo

Jeon

Kwon

et al. 2023

Adv Healthcare Materials

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The recent development of RNA-based therapeutics in delivering nucleic acids for gene editing and regulating protein translation has led to the effective treatment of various diseases including cancer, inflammatory and genetic disorder, as well as infectious diseases. Among these, lipid nanoparticles (LNP) have emerged as a promising platform for RNA delivery and have shed light by resolving the inherent instability issues of naked RNA and thereby enhancing the therapeutic potency. These LNP consisting of ionizable lipid, helper lipid, cholesterol, and poly(ethylene glycol)-anchored lipid can stably enclose RNA and help them release into the cells' cytosol. Herein, the significant progress made in LNP research starting from the LNP constituents, formulation, and their diverse applications is summarized first. Moreover, the microfluidic methodologies which allow precise assembly of these newly developed constituents to achieve LNP with controllable composition and size, high encapsulation efficiency as well as scalable production are highlighted. Furthermore, a short discussion on current challenges as well as an outlook will be given on emerging approaches to resolving these issues.

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Synthesis of Guanidines and Some of Their Biological Applications

Cited by 12 publications

References 130 publications

A bacterial spermidine biosynthetic pathway via carboxyaminopropylagmatine

A bacterial spermidine biosynthetic pathway via carboxyaminopropylagmatine

Química Orgânica: Conceitos, Fundamentos e Avanços

High‐Precision Synthesis of RNA‐Loaded Lipid Nanoparticles for Biomedical Applications

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