Guanidine Motif in Biologically Active Peptides

Abstract

In the past decade, guanidines have attracted attention as valuable hydrogen bond-based catalysts while they have long been considered as organic superbases with a broad scope of synthetic applicability. Their easy modification has also expanded their capacity to form complexes with a wide range of metal salts as effective metal scavengers. All these attractive aspects have promoted a huge growth in the field of organic synthesis involving guanidines and examples of such reactions have been collected in numerous reviews and some books. Moreover, this structural motif is also present in a large number of natural products and biologically active compounds that exhibit appealing properties and play important roles in medicinal chemistry. In this highlight, we will only cover the synthesis and properties of biologically active guanidine-containing peptides reported in the past 3 years.

Spatially Resolved Confocal Resonant Raman Microscopic Analysis of Anode‐Grown Geobacter sulfurreducens Biofilms

“…The guanidine functional group is ubiquitous in nature (as the primary functional group of arginine),1 and is also widely used in a synthetic setting for purposes such as enantioselective catalysis,2 anion recognition,3 and as a component of both natural4 and synthetic antimicrobial agents 5. A number of recent reviews highlight the preparation of guanidines using transition‐metal catalysis and carbodiimide‐based reagents 6.…”

Facile Synthesis of Guanidine Functionalised Building Blocks

“…[6] Nevertheless a great number of widely used non-catalytic protocols exist and these typically employ tertbutoxycarbonyl (Boc) protected guanidinylating agents [7] ( Figure 1) such as a N,Nʹ-bis(Boc)thiourea (1), [8] N,Nʹ-bis(Boc)-Smethylisothiourea (2), [9] N,Nʹ-bis(Boc)-Nʺ-triflylguanidine (3), [10] N,Nʹ-bis(Boc)-1H-pyrazole-1-carboxamidine (4) [11] and N,Nʹ-bis(Boc)benzotriazolecarboxamidine (5). [12] In some instances the guanidinylating agent ( Figure 1) must be synthesised before use as they are not commercially available (5), and others are somewhat expensive (3). Although pyrazole 4 has proven to be a useful guanidinylating agent, its synthesis typically requires two separate Boc protecting steps.…”

“…The guanidine functional group is ubiquitous in nature (as the primary functional group of arginine amino acids), [1] and is also widely used in a synthetic setting for purposes such as enantioselective catalysis, [2] anion recognition [3] and as components of both natural [4] and synthetic antimicrobial agents. [5] A number of recent reviews highlight the preparation of guanidines using transition metal catalysis and carbodiimide based reagents.…”

The Chemistry of Guanidine, Guanidinium, and Guanidinate Compounds

“…We wish to highlight the review articles contained herein, dealing with the subjects of guanidines in biologically active peptides, [10] the application of guanidine compounds in the capture and fixation of CO 2 , [34] guanidinates as ligands in chemical vapour deposition (CVD) and atomic layer deposition (ALD) applications, [36] and multiply bonded metal-metal compounds supported by bicyclic guanidinates as strong reducing agents. [29] We hope that these will be a valuable resource for those working in the respective areas.…”

“…It is well known for interacting with anionic groups such as phosphates, nucleotide bases, and carboxylatecontaining biomolecules through hydrogen bonding. Thus the guanidine group has an important role in biological systems, [10] and new routes to the synthesis of guanidine-containing compounds remains an important topic. [11] This naturally occurring affinity for a host of anions and propensity to form strong hydrogen bonds have led to the development of guanidines, and their cationic guanidinium cations, as tectons employed by crystal engineers in supramolecular chemistry.…”