Synthesis of trifunctional cyclo-β-tripeptide templates

• Frank Stein,
• Tahir Mehmood,
• Tilman Plass,
• Javid H. Zaidi and
• Ulf Diederichsen

Beilstein J. Org. Chem. 2012, 8, 1576–1583, doi:10.3762/bjoc.8.180

• demanding due to solution-phase synthesis of the β-tripeptides and their final cyclization with low efficiency [8][9]. Moreover, only homofunctionalized cyclic β-tripeptides have been described so far [9][10]. To further investigate and exploit the potential of this class of circular peptides, a synthetic

Polyionic polymers – heterogeneous media for metal nanoparticles as catalyst in Suzuki–Miyaura and Heck–Mizoroki reactions under flow conditions

• Klaas Mennecke and
• Andreas Kirschning

Beilstein J. Org. Chem. 2009, 5, No. 21, doi:10.3762/bjoc.5.21

• processes creates an ideal setup for an automated solution-phase synthesis. Furthermore, this combination of enabling techniques has great potential in the production of fine chemicals [7][8]. In continuation of our efforts in developing immobilization concepts for reagents and catalysts including

The first preparative solution phase synthesis of melanotan II

• Vladimir V. Ryakhovsky,
• Georgy A. Khachiyan,
• Nina F. Kosovova,
• Elena F. Isamiddinova and
• Andrey S. Ivanov

Beilstein J. Org. Chem. 2008, 4, No. 39, doi:10.3762/bjoc.4.39

• stimulating the skin tanning process. In this paper we report the first solution phase synthesis of the title compound. The hexapeptide sequence has been assembled by [(2+2)+1+1] scheme. After removing the orthogonal protection, a carbodiimide mediated lactamization, involving the ε-amino group of lysine and

• accomplished in 12 steps with 2.6% overall yield, affording >90% pure peptide without using preparative chromatography. Keywords: melanotan II; solution phase synthesis; peptide synthesis; Introduction Development of solid phase peptide synthesis methodology [1], recombinant techniques for expressing

• peptide pharmaceuticals are currently produced by chemical synthesis in solution including oxytocin, adrenocorticotropic hormone (ACTH), desmopressin, leuprolide, goserelin, and octreotide [6]. There is no account of a solution phase synthesis of melanotan II. The present paper describes a classical

A practical synthesis of the ¹³C/¹⁵N- labelled tripeptide N-formyl- Met-Leu-Phe, useful as a reference in solid- state NMR spectroscopy

• Sven T. Breitung,
• Jakob J. Lopez,
• Gerd Dürner,
• Clemens Glaubitz,
• Michael W. Göbel and
• Marcel Suhartono

Beilstein J. Org. Chem. 2008, 4, No. 35, doi:10.3762/bjoc.4.35

• cleavage process, EDT and TIS were added as scavengers [23][24]. Conclusion Compared to the solution phase synthesis of peptides, the solid phase synthesis offers a simplified purification of the intermediates. With the improved synthetic protocol based on Fmoc building blocks, where all reaction steps