177906-34-2

Upstream product

• 177906-31-9 3-[(3-Azido-propyl)-benzyloxycarbonyl-amino]-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester 
• 177906-28-4 3-[Benzyloxycarbonyl-(3-methanesulfonyloxy-propyl)-amino]-propionic acid methyl ester 
• 1476-39-7 1,5-diaminopentane dihydrochloride 
• 10494-79-8 methyl N-(3-hydroxypropyl)-β-alaninate 
• 177906-33-1 [(S)-1-(5-{3-[(3-Azido-propyl)-benzyloxycarbonyl-amino]-propionylamino}-pentylcarbamoyl)-2-carbamoyl-ethyl]-carbamic acid tert-butyl ester 

Downstream Products

• 177906-37-5 (3-Azido-propyl)-[2-(5-{(S)-2-[2-(2,4-bis-benzyloxy-phenyl)-acetylamino]-3-carbamoyl-propionylamino}-pentylcarbamoyl)-ethyl]-carbamic acid benzyl ester 
• 177906-36-4 (3-Azido-propyl)-[2-(5-{(S)-2-[2-(4-benzyloxy-phenyl)-acetylamino]-3-carbamoyl-propionylamino}-pentylcarbamoyl)-ethyl]-carbamic acid benzyl ester 
• 1026030-33-0 (3-Azido-propyl)-[2-(5-{(S)-3-carbamoyl-2-[2-(3-hydroxy-phenyl)-acetylamino]-propionylamino}-pentylcarbamoyl)-ethyl]-carbamic acid benzyl ester 

Relevant academic research and scientific papers

Syntheses and biological activities of joro spider toxin analogs to spidamine and joramine

In order to study the structure-activity relationships of spidamine and joramine found in the venom of Joro spider, Nephila clavata, we attempted to synthesize various analogs. Six analogs were convergently synthesized according to our previous method for the synthesis of spidamine, N-(3- aminopropyl-β-alanyl)-N'-(2,4-dihydroxyphenylacetyl-L-asparaginyl)-1,5- pentanediamine and joramine, N-(3-aminopropyl-β-alanyl)-N'-(4- hydroxyphenylacetyl-L-asparaginyl)-1,5-pentanediamine. The biological activities of the analogs and four intermediates were compared with those of synthetic spidamine and joramine in three bioassay systems, lobster neuromuscular synapse, cockroaches and mosquito larvae. The glutamate receptors in these systems were inhibited by some analogs, and the D- asparagine- or indoleacetyl-containing analogs were found to be strong inhibitors. These compounds have potential application as insecticides.

Total syntheses of spidamine and joramine, polyamine toxins from the joro spider, Nephila clavata

In order to confirm the structures of spidamine and joramine, identified from the venom of a spider (nephila clavata), we convergently synthesized both compounds, which have a common side chain of N-(L-asparaginyl)-N'-(3- aminopropyl-β-alanyl)-1,5-pentanediamine. A synthon of the common side chain was synthesized by starting with n-propanolamine which was converted to 7- azido-N-benzyloxycarbonyl-4-azaheptanoic acid N-hydroxysuccinimidyl ester. The ester was coupled with tert-butyloxycarbonyl-L-asparaginyl-1,5- pentanediamine to give the synthon of the common side chain. In the final synthesis of spidamine, the synthon of the common side chain was reacted with 2,4-dibenzyloxyphenylacetic acid N-hydroxysuccinimidyl ester, obtained by Willgerodt-kindler reaction of 2,4-dihydroxyacetophenone. The protected spidamine was catalytically hydrogenated to remove protective groups, affording spidamine itself in 13% yield from n-propanolamine. In the final synthesis of joramine, the synthon of the common side chain was reacted with 4-benzyloxyphenyl acetic acid N-hydroxysuccinimidyl ester. The protected joramine was also catalytically hydrogenated to produce joramine itself in 11% yield. The conformations of both synthesized compounds were analyzed by 1H-NMR and 13C-NMR. Their blocking activities on glutamate receptors were examined using lobster neuromuscular synapses.