Journal ArticleDOI
Peptide synthesis by a combination of solid-phase and solution methods II synthesis of fully protected peptide fragments on 2-methoxy-4-alkoxy-benzyl alcohol resin
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TLDR
In this paper, the synthesis of fully protected peptide fragments by the Fmoc/ t-butyl method on a new polymeric support is described, which is obtained in good yields and high purity upon cleavage from the resin with 0.5 - 1 % trifluoroacetic acid in methylene chloride.About:
This article is published in Tetrahedron Letters.The article was published on 1988-01-01. It has received 81 citations till now. The article focuses on the topics: Peptide synthesis & Trifluoroacetic acid.read more
Citations
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Solid phase peptide synthesis utilizing 9‐fluorenylmethoxycarbonyl amino acids
Gregg B. Fields,Richard L. Noble +1 more
TL;DR: The great variety of conditions under which Fmoc solid phase peptide synthesis may be carried out represents a truly "orthogonal" scheme, and thus offers many unique opportunities for bioorganic chemistry.
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Synthetic therapeutic peptides: science and market.
TL;DR: This review reports on the unexpected and considerable number of peptides that are currently available as drugs and the chemical strategies that were used to bring them into the market.
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Large-scale manufacture of peptide therapeutics by chemical synthesis
TL;DR: The large-scale commercial production of a 36-amino-acid peptide by chemical synthesis has been demonstrated in the development of enfuvirtide (T-20 or Fuzeon), a first-in-class membrane fusion inhibitor for the treatment of HIV.
Journal ArticleDOI
Methods and protocols of modern solid phase Peptide synthesis.
TL;DR: Essential protocols for the synthesis of fully deprotected peptides are presented including resin handling, coupling, capping, Fmoc-deprotection, final cleavage and disulfide bridge formation.
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2-Chlorotrityl chloride resin. Studies on anchoring of Fmoc-amino acids and peptide cleavage.
TL;DR: Under these exceptionally mild conditions 2-chlorotrityl cations generated during the cleavage of amino acids and peptides from resin do not attack the nucleophilic side chains of Trp, Met, and Tyr.
References
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Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides
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Solid phase synthesis without repetitive acidolysis. Preparation of leucyl-alanyl-glycyl-valine using 9-fluorenylmethyloxycarbonylamino acids.
TL;DR: The utility of repetitive nonhydrolytic base cleavage of alpha-amino protective groups in solid phase peptide synthesis is shown by a preparation of the model tetrapeptide leucyl-alanyl-glycyl-valine on a p-benZyloxybenzyl ester polystyrene--1% divinylbenzene resin support.
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Diketopiperazine Formation in Solid Phase Peptide Synthesis Using p‐Alkoxybenzyl Ester Resins and FMOC‐Amino Acids.
TL;DR: Diketopiperazine formation rates under the usual conditions of a solid phase peptide synthesis cycle with Fmoc-amino acids have been studied on a p -alkoxybenzyl ester resin.
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Sequence of the immunodominant epitope for the surface protein on sporozoites of Plasmodium vivax.
Thomas F. McCutchan,Altaf A. Lal,Vidal F. de la Cruz,Louis H. Miller,W. Lee Maloy,Yupin Charoenvit,Richard L. Beaudoin,Patricia Guerry,Richard Wistar,Stephen L. Hoffman,Wayne T. Hockmeyer,William E. Collins,Dyann F. Wirth +12 more
TL;DR: The structure of the immunodominant repeating peptide of the circumsporozoite (CS) protein of P. vivax was determined and it is indicated that the CS repeat is nine amino acids in length (Gly-Asp-Arg-Ala-AsP-Gally-Gln-Pro-AlA).
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STABLE ISOLATED SYMMETRICAL ANHYDRIDES OF Nα-9-FLUORENYLMETHYLOXYCARBONYLAMINO ACIDS IN SOLID-PHASE PEPTIDE SYNTHESIS:
TL;DR: The synthesis and isolation of symmetrical anhydrides of N alpha-9-fluorenylmethyloxycarbonyl (Fmoc) amino acids using water soluble carbodiimide is described, and these compounds were used in a solid phase peptide synthesis of methionine-enkephalin on a p-benZyloxybenzyl ester polystyrene 1% divinylbenzene resin support.