Facile Synthesis of Cyclic Tetrapeptides from Nonactivated Peptide Esters on Metal Centers

Haas, Katharina; Ponikwar, Werner; Nöth, Heinrich; Beck, Wolfgang

doi:10.1002/(sici)1521-3773(19980504)37:8<1086::aid-anie1086>3.0.co;2-v

Cited by 73 publications

(32 citation statements)

References 9 publications

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“…One of the first examples of the use of metal ions to conformationally preorganize a peptide for macrocyclization was demonstrated by Beck and co-workers 51 (Fig. 3a).…”

Section: Metal-ion-assisted Cyclizationsmentioning

confidence: 99%

Contemporary strategies for peptide macrocyclization

2011

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Peptide macrocycles have found applications that range from drug discovery to nanomaterials. These ring-shaped molecules have shown remarkable capacity for functional fine-tuning. Such capacity is enabled by the possibility of adjusting the peptide conformation using the techniques of chemical synthesis. Cyclic peptides have been difficult, and often impossible, to prepare using traditional synthetic methods. For macrocyclization to occur, the activated peptide must adopt an entropically disfavoured pre-cyclization conformation before forming the desired product. Here, we review recent solutions to some of the major challenges in this important area of contemporary synthesis.

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“…One of the first examples of the use of metal ions to conformationally preorganize a peptide for macrocyclization was demonstrated by Beck and co-workers 51 (Fig. 3a).…”

Section: Metal-ion-assisted Cyclizationsmentioning

confidence: 99%

Contemporary strategies for peptide macrocyclization

2011

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“…It was reported that different-membered cyclic tetrapeptides or macrolactams were synthesized from non-activated dipeptide ester precursors. The cyclization was carried out in methanol in the presence of sodium methoxide as base and with Ni 2+ , Pd 2+ or Cu 2+ as template (9).…”

Section: Introductionmentioning

confidence: 99%

Cyclization of several linear penta‐ and heptapeptides with different metal ions studied by CD spectroscopy^*

Liu

Youqi

Fan

et al. 2005

The Journal of Peptide Research

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A cyclic pentapeptide c(Tyr-Leu-Ala-Gly-Pro) (I), which was isolated and identified from Pseudostellaria heterophylla medicinal herbs, and two cyclic heptapeptides, c(Gly-Tyr-Gly-Gly-Pro-Phe-Pro) (II) and c(Gly-Ile-Pro-Tyr-Ile-Ala-Ala) (III), which were isolated and identified from Stellaria yunnanensis Franch (M), were synthesized by using 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3 H)-one (DEPBT) as a coupling reagent in solution, and mediated by different metal ions, from their linear peptide precursors H-Tyr-Leu-Ala-Gly-Pro-OH (I-1) and H-Ala-Gly-Pro-Tyr-Leu-OH (I-2), H-Gly-Tyr-Gly-Gly-Pro-Phe-Pro-OH (II-1) and H-Gly-Ile-Pro-Tyr-Ile-Ala-Ala-OH (III-1), respectively. The results show that alkali metal ions can improve the cyclization yields and/or the cyclization rates of linear peptide precursors, such as Na(+) ion is favorable for the cyclization of linear pentapeptides and Cs(+) ion is favorable for the cyclization of linear heptapeptides, while some bivalent and trivalent metal ions, such as Mg(2+), Ca(2+), Zn(2+), Fe(2+), Ni(2+) and Cr(3+) reduced/inhibited both the cyclization yields and the cyclization rates of the linear peptide precursors. The circular dichroism spectra of I-1, II-1 and III-1 with different metal ions were studied to elucidate the changes in their secondary structures. It is shown that Cs(+) can induce and stabilize the type I beta-turn conformation in the linear heptapeptide II-1 and the type II beta-turn conformation in the linear heptapeptide III-1.

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“…319 The ability of coordinating transition metals (Ni(II), Cu(II), Pd(II)) to simultaneously dimerize two acylic peptides in a 'head-to-tail' fashion to afford 12-18-membered cyclic peptides is particularly noteworthy. 344 Houghten and coworkers have employed imidazole as a nucleophilic catalyst to mediate the head-to-tail cyclization of peptide thioesters to afford cyclic peptides containing 5-11 amino acids, 345 whereas treatment of peptide thioacids with Sanger's reagent (1-fluoro-2,4-difluorobenzene) has been used for cyclization of penta-and hexapeptides. 346 ingenious ligation approach employing tert-butylisonitrile and an aziridine aldehyde to facilitate macrocyclization of linear tripeptides to afford cyclic peptides that contain reactive aziridine groups that can be derivatized as required.…”

Section: Phmentioning

confidence: 99%

6.11 N-Acylation Reactions of Amines

Taylor

Bull

2014

Comprehensive Organic Synthesis II

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Facile Synthesis of Cyclic Tetrapeptides from Nonactivated Peptide Esters on Metal Centers

Cited by 73 publications

References 9 publications

Contemporary strategies for peptide macrocyclization

Contemporary strategies for peptide macrocyclization

Cyclization of several linear penta‐ and heptapeptides with different metal ions studied by CD spectroscopy^*

6.11 N-Acylation Reactions of Amines

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Facile Synthesis of Cyclic Tetrapeptides from Nonactivated Peptide Esters on Metal Centers

Cited by 73 publications

References 9 publications

Contemporary strategies for peptide macrocyclization

Contemporary strategies for peptide macrocyclization

Cyclization of several linear penta‐ and heptapeptides with different metal ions studied by CD spectroscopy*

6.11 N-Acylation Reactions of Amines

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Resources

About

Cyclization of several linear penta‐ and heptapeptides with different metal ions studied by CD spectroscopy^*