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Literature DB >> 34550575

Fmoc Solid Phase Peptide Synthesis of Oxytocin and Analogues.

Thomas Kremsmayr¹, Markus Muttenthaler^2,3.

Abstract

Solid phase peptide synthesis is the most commonly used method for the production of peptides. In this chapter, we outline the standard operating procedures used in our laboratory to efficiently access oxytocin-like peptides. This includes detailed descriptions of equipment setup, reagent selection, peptide assembly on solid support, peptide side chain deprotection and cleavage from the solid support, oxidative folding, purification, and analysis.

Entities: Chemical

Keywords: 9-fluorenylmethoxycarbonyl (Fmoc); Amino acid coupling; Fmoc-SPPS; Oxidative peptide folding; Solid phase peptide synthesis (SPPS); Synthetic oxytocin analogues

Mesh：

Substances：

Year: 2022 PMID： 34550575 DOI： 10.1007/978-1-0716-1759-5_11

Source DB: PubMed Journal: Methods Mol Biol ISSN： 1064-3745

33 in total

1. In situ neutralization in Boc-chemistry solid phase peptide synthesis. Rapid, high yield assembly of difficult sequences.

Authors: M Schnölzer; P Alewood; A Jones; D Alewood; S B Kent
Journal: Int J Pept Protein Res Date: 1992 Sep-Oct

Review 2. Solid phase peptide synthesis utilizing 9-fluorenylmethoxycarbonyl amino acids.

Authors: G B Fields; R L Noble
Journal: Int J Pept Protein Res Date: 1990-03

3. Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides.

Authors: E Kaiser; R L Colescott; C D Bossinger; P I Cook
Journal: Anal Biochem Date: 1970-04 Impact factor: 3.365

4. Quantitative monitoring of solid-phase peptide synthesis by the ninhydrin reaction.

Authors: V K Sarin; S B Kent; J P Tam; R B Merrifield
Journal: Anal Biochem Date: 1981-10 Impact factor: 3.365

5. Methods, setup and safe handling for anhydrous hydrogen fluoride cleavage in Boc solid-phase peptide synthesis.

Authors: Markus Muttenthaler; Fernando Albericio; Philip E Dawson
Journal: Nat Protoc Date: 2015-06-18 Impact factor: 13.491

6. Solid-phase peptide synthesis using mild base cleavage of N alpha-fluorenylmethyloxycarbonylamino acids, exemplified by a synthesis of dihydrosomatostatin.

Authors: C D Chang; J Meienhofer
Journal: Int J Pept Protein Res Date: 1978-03

Fmoc Solid Phase Peptide Synthesis of Oxytocin and Analogues.

1. In situ neutralization in Boc-chemistry solid phase peptide synthesis. Rapid, high yield assembly of difficult sequences.

Review 2. Solid phase peptide synthesis utilizing 9-fluorenylmethoxycarbonyl amino acids.

3. Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides.

4. Quantitative monitoring of solid-phase peptide synthesis by the ninhydrin reaction.

5. Methods, setup and safe handling for anhydrous hydrogen fluoride cleavage in Boc solid-phase peptide synthesis.

6. Solid-phase peptide synthesis using mild base cleavage of N alpha-fluorenylmethyloxycarbonylamino acids, exemplified by a synthesis of dihydrosomatostatin.

7. HBTU activation for automated Fmoc solid-phase peptide synthesis.

Review 8. Amide bond formation: beyond the myth of coupling reagents.

Review 9. Advances in Fmoc solid-phase peptide synthesis.

Review 10. Automated solid-phase peptide synthesis to obtain therapeutic peptides.

1. Approaches to Improve the Quantitation of Oxytocin in Human Serum by Mass Spectrometry.

2. On the Utility of Chemical Strategies to Improve Peptide Gut Stability.