Document Detail


Repetitive BOP coupling (REBOP) in solid phase peptide synthesis. Luliberin synthesis as model.
MedLine Citation:
PMID:  2198236     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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.
Authors:
R Seyer; A Aumelas; A Caraty; P Rivaille; B Castro
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
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:
Created Date:  1990-09-04     Completed Date:  1990-09-04     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0330420     Medline TA:  Int J Pept Protein Res     Country:  DENMARK    
Other Details:
Languages:  eng     Pagination:  465-72     Citation Subset:  IM    
Affiliation:
CNRS-INSERM, Center of Pharmacology-Endocrinology, Montpellier, France.
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MeSH Terms
Descriptor/Qualifier:
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:
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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