15109-75-8

Upstream product

• 37963-39-6 (S)-1-((R)-2-{(S)-2-[(S)-5-Benzyloxycarbonylamino-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-pentanoylamino]-4-methyl-pentanoylamino}-3-phenyl-propionyl)-pyrrolidine-2-carboxylic acid 2,5-dioxo-pyrrolidin-1-yl ester 
• 917501-49-6 Boc-D-Phe-Pro-Val-Orn(Z)-OH 

Relevant academic research and scientific papers

Biomimetic formation of gramicidin S by dimerization-cyclization of pentapeptide precursor on solid support

The biomimetic formation of gramicidin S, cyclo(-d-Phe-Pro-Val-Orn-Leu-)2, by the dimerization and cyclization of pentapeptide precursor without the protection of δ-amino group of the Orn residue was examined on a solid support. The cyclization of H-d-Phe-Pro-Val-Orn-Leu-oxime on a resin with an oxime group of 0.62 mmol/g in 1,4-dioxane directly gave gramicidin S in a 50% yield. The dimerization-cyclization mode on the solid support was similar to that of the biosynthesis of gramicidin S on an enzyme.

FACILE SYNTHESIS OF GRAMICIDIN S VIA CYCLIZATION OF A LINEAR PENTAPEPTIDE

Azide and N-hydroxysuccinimide ester of five pentapeptides related to gramicidin S (cyclic decapeptide) were cyclized to determine the ratio of dimer to monomer in the cyclization product, the pentapeptide dervative with D-Phe as C-terminus giving the dimer in good yield.