221689-43-6

Basic information

• Product Name: N-Fmoc-Ile-Ile-Pro-Tyr(OBu^t)-Pro-Phe-Pro-OBu^t
• CAS NO: 221689-43-6
• Molecular Weight: 1180.49
• Mol File: 221689-43-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-Fmoc-Ile-Ile-Pro-Tyr(OBu^t)-Pro-Phe-Pro-OBu^t(CAS DataBase Reference)
• NIST Chemistry Reference: N-Fmoc-Ile-Ile-Pro-Tyr(OBu^t)-Pro-Phe-Pro-OBu^t(221689-43-6)
• EPA Substance Registry System: N-Fmoc-Ile-Ile-Pro-Tyr(OBu^t)-Pro-Phe-Pro-OBu^t(221689-43-6)

Safety Data

• Hazardous Substances Data: 221689-43-6(Hazardous Substances Data)

Upstream product

• 71989-31-6 Fmoc-Pro-OH 
• 35661-40-6 N-Fmoc L-Phe 
• 129472-19-1 (9H-fluoren-9-yl)methyl tert-butylpyrrolidine-1,2-dicarboxylate 
• 160464-32-4 N-Fmoc-Phe-Pro-OBu^t 
• 175548-78-4 N-Fmoc-Ile-Pro-OBu^t 
• 221689-32-3 N-Fmoc-Ile-Ile-Pro-OBu^t 
• 221689-40-3 N-Fmoc-Tyr(OBu^t)-Pro-Phe-Pro-OBu^t 
• 71989-23-6 Fmoc-Ile-OH 

Relevant articles and documents

Antineoplastic agents. 400. Synthesis of the Indian ocean marine sponge cyclic heptapeptide phakellistatin 2

Solution-phase synthesis of the marine sponge constituent phakellistatin 2 (1), cyclo(Tyr-Pro-Phe-Pro-Ile-Ile-Pro), was completed using a combination of stepwise coupling and (4 + 3) segment condensation. Use of diethyl phosphorocyanidate for the peptide bond formations gave the linear heptapeptide in 54% yield. Cyclization was achieved in high yields utilizing TBTU (2), BOP-C1 (3), PyBroP (4), and HOAt (5), resulting in 50-65% yields of phakellistatin 2 (1) depending on the method employed. The synthetic cyclic peptide was chemically but not biologically identical with the natural product.