34994-11-1

Usage

Uses

Used in Pharmaceutical Industry:
Hypusine is used as a key component in the development of drugs targeting cell growth and division. Its presence in specific proteins allows for the modulation of their activity, making it a potential therapeutic target for conditions related to abnormal cell proliferation, such as cancer.
Used in Research and Development:
Hypusine is utilized as a research tool for studying the role of eukaryotic initiation factor 5A (eIF5A) and its hypusine-containing variants in cellular processes. Understanding the function and regulation of these proteins can provide insights into various biological pathways and contribute to the development of novel therapeutic strategies.
Used in Diagnostic Applications:
Hypusine can be employed as a biomarker for certain diseases, particularly those involving altered cell growth or division. Detecting changes in hypusine levels or its associated proteins may help in the diagnosis, prognosis, or monitoring of disease progression.

InChI:InChI=1/C10H23N3O3/c11-5-4-8(14)7-13-6-2-1-3-9(12)10(15)16/h8-9,13-14H,1-7,11-12H2,(H,15,16)/t8-,9-/m0/s1

Upstream product

• 87681-49-0 (S)-2-Benzyloxycarbonylamino-6-{[(R)-2-((R)-1-phenyl-ethyl)-isoxazolidin-5-ylmethyl]-amino}-hexanoic acid benzyl ester 
• 87681-51-4 (S)-2-Benzyloxycarbonylamino-6-{[1-[(R)-2-((R)-1-phenyl-ethyl)-isoxazolidin-5-yl]-meth-(E)-ylidene]-amino}-hexanoic acid benzyl ester 
• 5591-94-6 N^(α)-benzyloxycarbonyl-L-lysine benzyl ester 
• 143565-78-0 tert-butyl 2(S)-(1,3-dibenzylhexahydro-2-oxo-1,3,5-triazin-5-yl)-6-oxohexanoate 
• 143565-66-6 (E)-(S)-2-(3,5-Dibenzyl-4-oxo-[1,3,5]triazinan-1-yl)-6-oxo-hex-4-enoic acid tert-butyl ester 
• 151963-67-6 (2S,9S)-7-Benzyl-2-(carbobenzoxyamino)-10-chloro-9-hydroxy-7-azadecanoic acid benzyl ester 
• 78767-79-0 N^ε-benzyl-N^α-carbobenzoxy-L-lysine benzyl ester 
• 5361-91-1 N_α-benzyloxycarbonyl-L-lysine benzyl ester p-toluenesulfonate 
• 151963-69-8 (2S,9R)-7-Benzyl-2-(carbobenzoxyamino)-10-cyano-9-hydroxy-7-azadecanoic acid benzyl ester 
• 82267-37-6 (S)-2-Benzyloxycarbonylamino-6-((R)-4-benzyloxycarbonylamino-2-hydroxy-butylamino)-hexanoic acid benzyl ester 
• 143565-82-6 tert-butyl 7-aza-2(S)-<(tert-butoxycarbonyl)amino>-11-(1,3-dibenzylhexahydro-2-oxo-1,3,5-triazin-5-yl)-9(R)-hydroxyundecanoate 

Relevant academic research and scientific papers

Total Syntheses of (+)-Hypusine and Its (2S,9S)-Diastereomer

The total synthesis of (2S,9R)-hypusine dihydrochloride, an unusual amino acid constituent of the eukaryotic translation initiation factor eIF-4D, and its (2S,9S) diastereomer is described.The key step in the syntheses involves Nε-alkylation of Nε-benzyl-Nα-(L)-lysine benzyl ester with (R)- or (S)-epichlorhydrin to give the respective (2S,9R) and (2S,9S) chlorohydrins.Subsequent displacement of the respective chlorides by cyanide ion provides the protected hypusine skeletons.The final step, hydrogenation over PtO2 in AcOH followed by neutralization and reacidification, yielded the respective (2S,9S)- and (2S,9R)-hypusine dihydrochlorides in excess of 50percent overall yield.

Chemistry of Naturally Occurring Polyamines. 8. Total Synthesis of (+)-Hypusine

As part of a program to synthesize biologically interesting polyamines and their conjugates, we report a new approach to the synthesis of hypusine (1), an unusual amino acid constituent of the eucaryotic translation initiation factor elF-4D.Hypusine is fo

Synthesis and Stereochemistry of Hypusine, a New Amino Acid in Bovine Brain

Hypusine, a new basic amino acid occurring in the homogenate of bovine brain tissue, was synthesized to determine the absolute structure.Nα-Benzyloxycarbonyl-L-lysine benzyl ester was coupled with (S)- or (R)-4-benzyloxycarbonylamino-1-bromo-2-butanol derived from L- or D-malic acid, respectively.The products were deprotected by catalytic dehydrogenation.One of the synthetic compounds, i.e., (2S,9R)-2,11-diamino-9-hydroxy-7-azaundecanoic acid, was completely identical with natural hypusine in all respects.