Open AccessTotal synthesis of human beta-lipotropin.
Author(s) -
James Blake,
Choh Hao Li
Publication year - 1983
Publication title -
proceedings of the national academy of sciences of the united states of america
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.011
H-Index - 771
eISSN - 1091-6490
pISSN - 0027-8424
DOI - 10.1073/pnas.80.6.1556
Subject(s) - acetic anhydride , chemistry , isoelectric point , peptide , trypsin , isoelectric focusing , beta (programming language) , yield (engineering) , chromatography , radioimmunoassay , silver nitrate , dimethylformamide , acetic acid , biochemistry , organic chemistry , enzyme , materials science , solvent , computer science , metallurgy , programming language , catalysis
The total synthesis of human beta-lipotropin has been accomplished by the new segment-coupling method in aqueous solution. The peptides Ac-Arg-beta-lipotropin-(61-89) (I) and [GlyS60]-beta-lipotropin-(1-60) (II) were synthesized by the solid-phase method. Reaction of peptide I with citraconic anhydride followed by brief digestion with trypsin to remove the acetylarginyl group, gave Ia. Reaction of peptide II with citraconic anhydride gave the citraconyl peptide IIa. Ia and IIa were coupled together in 50% dimethylformamide by reaction with silver nitrate/N-hydroxysuccinimide. After removal of the citraconyl groups in 25% acetic acid, a 10% yield of synthetic beta-lipotropin could be isolated. The synthetic product was shown to be identical to native human beta-lipotropin by paper electrophoresis, isoelectric focusing, HPLC, lipolytic activity in isolated rabbit fat cells, and radioimmunoassay.