‘100 years of peptide synthesis’: ligation methods for peptide and protein synthesis with applications to <i>β</i>‐peptide assemblies*

Kimmerlin, Thierry; Seebàch, Dieter

doi:10.1111/j.1399-3011.2005.00214.x

Cited by 183 publications

(108 citation statements)

References 125 publications

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“…Besides this, it was shown that oxime ligation represents a highly efficient method for conjugation of various biomolecules [23][24][25][26]. Particularly, we and others have reported that aminooxy function can be easily incorporated to anomer position of sugars [27][28][29] and that this modification enables the quantitative coupling to peptide containing either aldehyde or ketone moieties [18,30,31].…”

Section: Resultsmentioning

confidence: 99%

A Fully Solid-Phase Synthesis of Biotinylated Glycoclusters

Renaudet¹,

Dumy²

2008

TOGLYJ

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Abstract:The fully solid-phase synthesis of chemically well-defined glycoclusters grafted to a topological cyclodecapeptide template is described. The orthogonally protected peptide backbone was first synthesized and cyclized on solid support using D-glutamic acid as first amino acid linked to the resin. After successive regioselective deprotection steps, biotins were coupled to the lower addressable domains of the scaffold, then carbohydrates-binding ligands were assembled as cluster on the upper domain using a chemoselective oxime-based strategy. This provides multitopic labeled glycopeptides which can be easily immobilized to streptavidin-coated surfaces for studying carbohydrate-protein interactions in glycomic researches.

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Section: Resultsmentioning

confidence: 99%

A Fully Solid-Phase Synthesis of Biotinylated Glycoclusters

Renaudet¹,

Dumy²

2008

TOGLYJ

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“…As expected, the methodology is rapidly being changed by evolving strategies that overcome some of the limitations of the process. 96 Several strategies have been tried, and based on their observations it was suggested that a Nlinked 2-mercaptobenzyl group could form the basis of a new peptide ligation chemistry ( Figure 42). The model requires tailoring the mercaptobenzyl skeleton for lability.…”

Section: Scheme 51mentioning

confidence: 99%

Evolution of amide bond formation

Joullié¹,

Lassen²

2010

Arkivoc

160

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This paper is dedicated to Drs Bruce E. Maryanoff and Cynthia A. Maryanoff for their outstanding contribution to organic chemistry as industrial chemists AbstractThe presence of carboxamide groups is found in a large array of biologically important compounds. Peptides and proteins play an important role in modern biology. A key step in peptide production is the formation of the peptide bond, which involves amide bond formation. Chemical synthesis of large peptides by intermolecular coupling of smaller peptides using conventional peptide bond-forming techniques did not realize its potential advantages until recently. Using an approach based on highly specific and efficient chemical ligation of two peptide segments, the two subunits were ligated to form a new peptide bond. Native chemical ligation extended the concept by creating a native peptide bond and providing new approaches to protein engineering.

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“…The centrality of the amide linkage, as found in polypeptides and proteins, in the maintenance of life hardly needs restatement. Numerous strategies, resulting in a vast array of protocols to synthesize biologically active polypeptides and proteins, have been demonstrated (3,4). Central to reiterative polypeptide bond formations was the discovery and remarkable development of solid-phase peptide synthesis (SPPS) (5,6).…”

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Solid-phase peptide synthesis and solid-phase fragment coupling mediated by isonitriles

Wang

2013

Proc. Natl. Acad. Sci. U.S.A.

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The synthesis of polypeptides on solid phase via mediation by isonitriles is described. The acyl donor is a thioacid, which presumably reacts with the isonitrile to generate a thio-formimidate carboxylate mixed anhydride intermediate. Applications of this chemistry to reiterative solid-phase peptide synthesis as well as solid-phase fragment coupling are described.A mide bond formations are arguably among the most important constructions in organic chemistry (1, 2). The centrality of the amide linkage, as found in polypeptides and proteins, in the maintenance of life hardly needs restatement. Numerous strategies, resulting in a vast array of protocols to synthesize biologically active polypeptides and proteins, have been demonstrated (3, 4). Central to reiterative polypeptide bond formations was the discovery and remarkable development of solid-phase peptide synthesis (SPPS) (5, 6). The extraordinary impact of SPPS in fostering enhanced access to homogeneous polypeptides is clear to everyone in the field.As we have described elsewhere, by classical, mechanistic reasoning, we were led to conjecture about some hithertounexplored possibilities relevant to the chemistry of isonitriles (7)(8)(9)(10)(11)(12)(13)(14). It was anticipated that isonitriles might be able to mediate the acylation of amines, thus giving rise to amides (15). Early experiments focused on free carboxylic acids as the acylating agents. As our studies progressed, it was found that the combination of thioacids, amines, and isonitriles leads to the efficient formation of amide bonds under stoichiometric or nearstoichiometric conditions (7-13, 16, 17). Although there remain unresolved issues of detail and nuance, the governing mechanism for amide formation under these conditions involves reaction of the thioacid, 1, with an isonitrile, 2, to generate a thio-formimidate carboxylate mixed anhydride (thio-FCMA), 3, which is intercepted by the "acyl-accepting" amine to generate amide, 5, and thioformamide, 6 (Fig. 1). The efficiency of the amidation was further improved through the use of hydroxybenzotriazole (HOBt) (18), which could well give rise to HOBt ester 7, although this pathway has not been mechanistically proven.The potentialities of the isonitrile-mediated amidation method were foreshadowed via its application to the synthesis of cyclosporine (19). The power of the method was particularly well demonstrated in the context of our recent total synthesis of oxytocin (OT) (20), wherein isonitrile mediation was used in each of the peptide bond constructions, leading to the synthesis of the hormone in high yield and excellent purity. This nonapeptide is involved in a range of biological functions including parturition and lactation (21,22). Signaling of OT to its receptor (OTR) is apparently an important factor in quality maintenance of various CNS functions (23). The ability to synthesize such modestly sized, but bio-impactful peptides in both native (wild-type) form, and as strategically modified variants, is one of the current missions of our labo...

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‘100 years of peptide synthesis’: ligation methods for peptide and protein synthesis with applications to β‐peptide assemblies*

Cited by 183 publications

References 125 publications

A Fully Solid-Phase Synthesis of Biotinylated Glycoclusters

A Fully Solid-Phase Synthesis of Biotinylated Glycoclusters

Evolution of amide bond formation

Solid-phase peptide synthesis and solid-phase fragment coupling mediated by isonitriles

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