Ribosomal Synthesis of Macrocyclic Peptides with β2- and β2,3-Homo-Amino Acids for the Development of Natural Product-Like Combinatorial Libraries

2021 ◽  
Author(s):  
Emel Adaligil ◽  
Aimin Song ◽  
Kenneth K. Hallenbeck ◽  
Christian N. Cunningham ◽  
Wayne J. Fairbrother
Keyword(s):  
Amino Acids ◽  
Natural Product ◽  
Combinatorial Libraries ◽  
Macrocyclic Peptides

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

scholarly journals Expanded toolbox for directing the biosynthesis of macrocyclic peptides in bacterial cells

2020 ◽  
Vol 11 (24) ◽  
pp. 6202-6208
Author(s):  
Jacob A. Iannuzzelli ◽  
Rudi Fasan
Keyword(s):  
Amino Acids ◽  
Unnatural Amino Acids ◽  
Bacterial Cells ◽  
Macrocyclic Peptides ◽  
Live Bacteria

A new suite of unnatural amino acids is reported for directing the biosynthesis of genetically encoded macrocyclic peptides in live bacteria.

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.

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.

Novel Cylindrical, Conical, and Macrocyclic Peptides from the Cyclooligomerization of Functionalized Thiazole Amino Acids

2001 ◽  
Vol 123 (2) ◽  
pp. 333-334 ◽  
Author(s):  
Yogendra Singh ◽  
Nikolai Sokolenko ◽  
Michael J. Kelso ◽  
Lawrence R. Gahan ◽  
Giovanni Abbenante ◽  
...  
Keyword(s):  
Amino Acids ◽  
Macrocyclic Peptides

scholarly journals Recent Advances in Substrate-Controlled Asymmetric Induction Derived from Chiral Pool α-Amino Acids for Natural Product Synthesis

Molecules ◽  
2016 ◽  
Vol 21 (7) ◽  
pp. 951 ◽  
Author(s):  
Seung-Mann Paek ◽  
Myeonggyo Jeong ◽  
Jeyun Jo ◽  
Yu Heo ◽  
Young Han ◽  
...  
Keyword(s):  
Amino Acids ◽  
Natural Product ◽  
Natural Product Synthesis ◽  
Asymmetric Induction ◽  
Recent Advances
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