189280-20-4

Upstream product

• 189280-15-7 tert-butyl(2S,9R)-11-[(benzyloxycarbonyl)amino]-2-[(tert-butoxycarbonyl)amino]-9-hydroxy-7-(benzyloxycarbonyl)-7-azaundecanoate 
• 501-53-1 benzyl chloroformate 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 

Downstream Products

• 189280-23-7 (2S,9R)-2-Amino-11-[(Benzyloxycarbonyl)amino]-7-(carbobenzyloxy)-9-(tetrahydropyran-2-yloxy)-7-azaundecanoic Acid 

Relevant academic research and scientific papers

Hypusine reagent for peptide synthesis

A derivative of hypusine useful as a reagent for synthesizing peptides containing hypusine, as well as an improved method for synthesizing the same, the derivative having the formula: wherein: Q1and Q2may be the same or different and

Synthesis of reagents for the construction of hypusine and deoxyhypusine peptides and their application as peptidic antigens

Two new synthetic methods which allow access to (2S)-deoxyhypusine, natural (2S,9R)-hypusine, (2S,9S)-hypusine, and deoxyhypusine- and hypusine- containing peptides are described. The methods involve both the construction of a deoxyhypusine reagent in which the α-nitrogen protecting group is orthogonal to the N-7 and N-12 protecting groups and an alternate synthesis of our previous hypusine reagent, a synthesis which provides for better stereochemical control at C-9. Synthetic hypusine and deoxyhypusine can be generated from these reagents. The hypusine-containing hexapeptide (Cys-Thr- Gly-Hpu-His-Gly) is conjugated to ovalbumin (OVA), keyhole limpet hemocyanin (KLH), and a bis-maleimide; KLH conjugates are also made with the deoxyhypusine- and lysine-containing hexapeptides. Monoclonal antibodies are generated to the hypusine-containing hexapeptide-OVA conjugate in mice. These are isolated and screened against the hypusine-containing hexapeptide-KLH and hypusine-containing hexapeptide-bis-maleimide conjugates, as well as against the deoxyhypusine-containing and lysine-containing hexapeptide-KLH conjugates. These antibodies may be useful in localizing intracellular hypusine-containing peptides as well as peptides containing hypusine analogues.

Development of a Hypusine Reagent for Peptide Synthesis

The synthesis of a reagent that enables the incorporation of the unusual amino acid (2S,9R)-hypusine (Hpu) into peptide sequences is described.The reagent, (2S,9R)-11--7-(carbobenzyloxy)-2--9-(tetrahydropyran-2-yloxy)-7-azaundecanoic acid, is utilized in the synthesis of a hexapeptide containing the primary pentapeptide sequence of the eukaryotic initiation factor eIF-5A, L-Cys-L-Thr-Gly-Hpu-L-His-Gly.The reagent is shown to be effective for both solution phase and Merrifield resin synthesis.