| Repetitive BOP coupling (REBOP) in solid phase peptide synthesis. Luliberin synthesis as model. | |
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MedLine Citation:
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PMID: 2198236 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The coupling reagent (benzotriazol-1-yloxy)tris-(dimethylamino)phosphonium (BOP) hexafluorophosphate was tested in the synthesis of luliberin (LH-RH) with inexpensive classically protected Boc-amino acids, in slight excess, and benzhydryl amino resin, without any other additive. The good solubility of this reagent and its by-products is of particular interest for automated peptide synthesis. [D-His2]LH-RH was also synthesized and compared with LH-RH by proton nuclear magnetic resonance spectroscopy. As shown by the biological tests and the high performance liquid chromatography study, unprotected pyroGlu and Boc-His can be used without any significant racemization but Boc-His(Boc) was found to be preferable since it gave no detectable racemization and no by-products. The difficult isolation of the minority D-derivative from the crude preparation of LH-RH was resolved by a recycling procedure in reversed phase HPLC. |
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Authors:
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R Seyer; A Aumelas; A Caraty; P Rivaille; B Castro |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: International journal of peptide and protein research Volume: 35 ISSN: 0367-8377 ISO Abbreviation: Int. J. Pept. Protein Res. Publication Date: 1990 May |
Date Detail:
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Created Date: 1990-09-04 Completed Date: 1990-09-04 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 0330420 Medline TA: Int J Pept Protein Res Country: DENMARK |
Other Details:
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Languages: eng Pagination: 465-72 Citation Subset: IM |
Affiliation:
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CNRS-INSERM, Center of Pharmacology-Endocrinology, Montpellier, France. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Amino Acid Sequence Gonadotropin-Releasing Hormone / chemical synthesis*, isolation & purification Indicators and Reagents* Molecular Sequence Data Organophosphorus Compounds* Peptides / chemical synthesis* Stereoisomerism |
| Chemical | |
Reg. No./Substance:
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0/Indicators and Reagents; 0/Organophosphorus Compounds; 0/Peptides; 33515-09-2/Gonadotropin-Releasing Hormone; 56602-32-5/benzotriazol-1-yloxy-tris(dimethylamino)phosphonium |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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