Advances in Fmoc solid‐phase peptide synthesis

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Advances in Fmoc solid‐phase peptide synthesis

Today, Fmoc SPPS is the method of choice for peptide synthesis. Very-high-quality Fmoc building blocks are available at low cost because of the economies of scale arising from current multiton production of therapeutic peptides by Fmoc SPPS. Many modified derivatives are commercially available as Fmoc building blocks, making synthetic access to a broad range of peptide derivatives straightforwa...

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Acid cleavage/deprotection in Fmoc/tBu solid-phase peptide synthesis.

In general, a solid-phase peptide synthesis (SPPS) consists of the assembly of a protected peptide chain on a polymeric support (=synthetic step) and the subsequent cleavage/deprotection to release the crude, deprotected peptide from the solid support (=cleavage step). Usually, these two steps are followed by chromatographic purification of the crude peptide (see Chapters 1,2,4, and 5, PAP). Th...

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Fast conventional Fmoc solid-phase peptide synthesis with HCTU.

1H-Benzotriazolium 1-[bis(dimethyl-amino)methylene]-5-chloro-hexafluorophosphate (1-),3-oxide (HCTU) is a nontoxic, nonirritating and noncorrosive coupling reagent. Seven biologically active peptides (GHRP-6, (65-74)ACP, oxytocin, G-LHRH, C-peptide, hAmylin(1-37), and beta-amyloid(1-42)) were synthesized with reaction times reduced to deprotection times of 3 min or less and coupling times of 5 ...

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N-Fmoc-Peptide azides: Synthesis, isolation, characterization and utility in the extension of peptide chains

The chemical approaches to the synthesis of peptides and proteins by the azide coupling 2 have turned out to be one of the safest methods of avoiding racemization. The azide procedure has been widely used for the coupling of difficult amino acid residues such as His, Thr, Ser, Trp, etc., and also particularly for the condensation of peptide fragments using both the maximum and minimum protectio...

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Cysteine Pseudoprolines for Thiol Protection and Peptide Macrocyclization Enhancement in Fmoc-Based Solid-Phase Peptide Synthesis

Contrary to other studies, here we describe cysteine (Cys) pseudoproline-containing peptides with short deprotection times in TFA. The deprotection times fell in the same range as other protecting groups commonly used in SPPS (e.g., 1-3 h). Moreover, when using Cys pseudoprolines as peptide macrocyclization-enhancing moieties a considerable reduction in reaction time was observed compared to a ...

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ژورنال

عنوان ژورنال: Journal of Peptide Science

سال: 2016

ISSN: 1075-2617,1099-1387

DOI: 10.1002/psc.2836