Stable Benzacridine Pigments by Oxidative Coupling of Chlorogenic Acid with Amino Acids and Proteins: Toward Natural Product-Based Green Food Coloring

2017 ◽  
Vol 65 (31) ◽  
pp. 6519-6528 ◽  
Author(s):  
Mariagrazia Iacomino ◽  
Fabian Weber ◽  
Maike Gleichenhagen ◽  
Valeria Pistorio ◽  
Lucia Panzella ◽  
...  
Keyword(s):  
Amino Acids ◽  
Chlorogenic Acid ◽  
Natural Product ◽  
Oxidative Coupling ◽  
Green Food

Peptide Modifications: Versatile Tools in Peptide and Natural Product Syntheses

Synlett ◽  
2019 ◽  
Vol 30 (11) ◽  
pp. 1289-1302 ◽  
Author(s):  
Phil Servatius ◽  
Lukas Junk ◽  
Uli Kazmaier
Keyword(s):  
Amino Acids ◽  
Natural Product ◽  
Bond Activation ◽  
Bond Formation ◽  
Side Chain ◽  
Peptide Backbone ◽  
Claisen Rearrangements ◽  
The Past ◽  
Allylic Alkylations ◽  
Peptide Modifications

Peptide modifications via C–C bond formation have emerged as valuable tools for the preparation and alteration of non-proteinogenic amino acids and the corresponding peptides. Modification of glycine subunits in peptides allows for the incorporation of unusual side chains, often in a highly stereoselective manner, orchestrated by the chiral peptide backbone. Moreover, modifications of peptides are not limited to the peptidic backbone. Many side-chain modifications, not only by variation of existing functional groups, but also by C–H functionalization, have been developed over the past decade. This account highlights the synthetic contributions made by our group and others to the field of peptide modifications and their application in natural product syntheses.1 Introduction2 Peptide Backbone Modifications via Peptide Enolates2.1 Chelate Enolate Claisen Rearrangements2.2 Allylic Alkylations2.3 Miscellaneous Modifications3 Side-Chain Modifications3.1 C–H Activation3.1.1 Functionalization via Csp3–H Bond Activation3.2.2 Functionalization via Csp2–H Bond Activation3.2 On Peptide Tryptophan Syntheses4 Conclusion

A new cyanine from oxidative coupling of chlorogenic acid with tryptophan: Assessment of the potential as red dye for food coloring

2021 ◽  
Vol 348 ◽  
pp. 129152
Author(s):  
Federica Moccia ◽  
María Ángeles Martín ◽  
Sonia Ramos ◽  
Luis Goya ◽  
Stefania Marzorati ◽  
...  
Keyword(s):  
Chlorogenic Acid ◽  
Oxidative Coupling ◽  
Red Dye

scholarly journals Functional and structural characterization of IdnL7, an adenylation enzyme involved in incednine biosynthesis

2019 ◽  
Vol 75 (4) ◽  
pp. 299-306
Author(s):  
Jolanta Cieślak ◽  
Akimasa Miyanaga ◽  
Makoto Takaishi ◽  
Fumitaka Kudo ◽  
Tadashi Eguchi
Keyword(s):  
Amino Acids ◽  
Substrate Specificity ◽  
Natural Product ◽  
Structural Characterization ◽  
Biochemical Analysis ◽  
Natural Product Biosynthesis ◽  
Broad Substrate Specificity ◽  
Selective Incorporation ◽  
Polyketide Antibiotic

Adenylation enzymes play an important role in the selective incorporation of the cognate carboxylate substrates in natural product biosynthesis. Here, the biochemical and structural characterization of the adenylation enzyme IdnL7, which is involved in the biosynthesis of the macrolactam polyketide antibiotic incednine, is reported. Biochemical analysis showed that IdnL7 selects and activates several small amino acids. The structure of IdnL7 in complex with an L-alanyl-adenylate intermediate mimic, 5′-O-[N-(L-alanyl)sulfamoyl]adenosine, was determined at 2.1 Å resolution. The structure of IdnL7 explains the broad substrate specificity of IdnL7 towards small L-amino acids.

N-Iodosuccinimide-Mediated Oxidative Coupling of Indoles and Phenols: A Synthetic Study toward the Benzofuroindoline Moiety of Bipleiophylline

Synthesis ◽  
2018 ◽  
Vol 50 (24) ◽  
pp. 4823-4828 ◽  
Author(s):  
Guillaume Vincent ◽  
Natacha Denizot ◽  
Régis Guillot ◽  
Cyrille Kouklovsky
Keyword(s):  
Natural Product ◽  
Oxidative Coupling

We report our efforts to apply an N-iodosuccinimide-mediated dearomative oxidative coupling of indoles and phenols to benzo­furoindoline-containing polycyclic scaffolds related to the natural product bipleiophylline. Suitable conditions from N-substituted indoles are developed and applied to the synthesis of a hexacyclic model starting from a tetracyclic ABCE precursor.

scholarly journals Antifeedant Activity of Spin-Labeled Derivatives of Deoxypodophyllotoxin against Brontispa longissima Larvae

2013 ◽  
Vol 8 (2) ◽  
pp. 1934578X1300800 ◽  
Author(s):  
Gang Feng ◽  
Jing Zhang ◽  
Liu Yang ◽  
Ying-Qian Liu ◽  
Zhi-Wei Zhang ◽  
...  
Keyword(s):  
Amino Acids ◽  
Natural Product ◽  
Antifeedant Activity ◽  
Podophyllotoxin Derivatives ◽  
Derivatives Of ◽  
Third Instar Larvae

To continue our search for natural product-based compounds for the control of Brontispa longissima larvae, eight spin-labeled podophyllotoxin derivatives (4a-h) and the intermediates 2 and 3 were tested for their insect antifeedant activity against third-instar larvae of B. longissima. Among all the tested compounds, 4a, 4c, 2 and 3 showed pronounced antifeedant activities with AFC50 values of 0.16, 0.31, 0.15 and 0.28 mg/mL, respectively. The different antifeedant activity ranges of these compounds indicated that variation of the structures of L-amino acids in these compounds markedly affected the activity profiles of this compound class, and some important SAR information has been revealed from it.

scholarly journals HISTOCHEMICAL DIFFERENTIATION BETWEEN TYROSINE AND CHLOROGENIC ACID IN PLANT TISSUES I. NITROUS ACID REACTIONS AND METAL CHELATION OF NITROSOTYROSINE

1968 ◽  
Vol 16 (3) ◽  
pp. 191-198 ◽  
Author(s):  
R. M. REEVE
Keyword(s):  
Amino Acids ◽  
Chlorogenic Acid ◽  
Nitrous Acid ◽  
Metal Chelate ◽  
Ultrastructural Localization ◽  
Plant Tissues ◽  
Metal Chelation ◽  
Copper Chelation ◽  
Acid Reaction ◽  
Color Reactions

Copper chelation of nitrosotyrosine has been found useful for histochemical localization for tyrosine in thick, fresh sections of large celled plant tissues. The nitrous acid reaction for ortho-dihydroxyphenolics also has been found useful for localization of chlorogenic acid, caffeic acid and dihydroxyphenylalanine in plant tissues. Application of these tests separately to serially adjacent sections demonstrated the distribution of tyrosine and chlorogenic acid in different plant tissues. Tests tube reactions on known substances verified specificity and also demonstrated that the presence of other amino acids and phenolics did not interfere with the positive test for tyrosine. The color reactions are sufficiently intense for stereoscopic microscopy and tested sections may be measured photometrically. Further adaptability of the nitrosotyrosine-metal chelate reaction to procedures for ultrastructural localization is suggested.

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