100017-93-4

Basic information

• Product Name: cyclo<-Arg(NO2)-Lys(Z)-Asp(OBzl)-Val-D-Tyr->
• Synonyms: cyclo<-Arg(NO2)-Lys(Z)-Asp(OBzl)-Val-D-Tyr->
• CAS NO: 100017-93-4
• Molecular Weight: 931.015
• Mol File: 100017-93-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: cyclo<-Arg(NO2)-Lys(Z)-Asp(OBzl)-Val-D-Tyr->(CAS DataBase Reference)
• NIST Chemistry Reference: cyclo<-Arg(NO2)-Lys(Z)-Asp(OBzl)-Val-D-Tyr->(100017-93-4)
• EPA Substance Registry System: cyclo<-Arg(NO2)-Lys(Z)-Asp(OBzl)-Val-D-Tyr->(100017-93-4)

Safety Data

• Hazardous Substances Data: 100017-93-4(Hazardous Substances Data)

Upstream product

• 13211-31-9 tert-butyl L-valinate 
• 68455-62-9 Boc-Arg(NO₂)-Lys(Z)-OMe 
• 100102-88-3 Boc-Arg(NO₂)-Lys(Z)-OH 
• 100102-93-0 H-Asp(OBzl)-Val-Tyr-OBu^t*TFA 
• 100102-91-8 Ddz-Asp(OBzl)-Val-Tyr-OBu^t 
• 100102-89-4 Z-Val-Tyr-OBu^t 
• 100102-90-7 H-Val-Tyr-OBu^t 
• 2188-18-3 N-alpha-t-butoxycarbonyl-Ng-nitroarginine 
• 16874-12-7 Tyr(tBu) 
• 1149-26-4 (S)-N-(benzyloxycarbonyl)valine 
• 100102-94-1 Boc-Arg(NO₂)-Lys(Z)-Asp(OBzl)-Val-Tyr-OBu^t 
• 97277-24-2 Boc-Tyr-Arg-NO₂-Lys-Z-Asp-OBzl-L-Val-X 
• 96356-48-8 Boc-Tyr-Arg(NO₂)-Lys(Z)-OMe 
• 96356-49-9 Boc-Tyr-Arg(NO₂)-Lys(Z)-OH 

Downstream Products

• 96356-59-1 cyclo<-Tyr-Arg-Lys-Asp-D-Val-> 
• 96356-59-1 (-Tyr-Arg-Lys-Asp-L-Val-)*2HOAc 
• 100164-85-0 cyclo<-Arg-Lys-Asp-Val-D-Tyr-> 

Relevant articles and documents

Cyclization of all-L-pentapeptides by means of 1-hydroxy-7-azabenzotriazole-derived uronium and phosphonium reagents

Due to their restricted conformational flexibility, cyclic peptides are of great interest in connection with structure-activity relationships, especially the elucidation of bioactive conformations. For linear peptides that do not contain turn structure-inducing amino acid residues, the cyclization reaction may be an inherently improbable or slow process, and side reactions, such as cyclodimerization and epimerization at the C-terminal residue, may dominate. A number of 1-hydroxy-7-azabenzotriazole-based onium salts were examined for cyclization of thymopentin-derived pentapeptides and the results compared with data from more conventional coupling reagents. The azabenzotriazol-derived coupling reagents stood out as being the most effective by far. The cyclizations proceed extremely rapidly, and in contrast to other coupling reagents, C-terminal epimerization was generally less than 10%. C-terminal D-amino acid residues favor the formation of monocyclic pentapeptide rings. A similar effect was observed for cyclization of linear N-methylamino acid-containing peptides, suggesting that reversible amide bond alkylation such as Hmb-modification should be useful in promoting the cyclization of pepitdes devoid of turn-inducing amino acid residues.

SYNTHESIS AND NMR INVESTIGATION OF CYCLIC PENTAPEPTIDE ANALOGUES OF THYMOPENTIN

The synthesis of two cyclic pentapeptides cyclo(-Arg-Lys-Xxx-D-Val-Tyr-) (Xxx= Asp or Glu) with thymopentin-analogue sequences is described.Cyclization was achieved by the carbodiimide/DMAP method.The results of the NMR investigations performed on the pro