938075-92-4

Basic information

• Product Name: N-((S)-1-(1,1-dimethylethoxycarbonyl)-5-oxopyrrolidine-2-carbonyl)-L-valine pentafluorophenyl ester
• Synonyms: N-((S)-1-(1,1-dimethylethoxycarbonyl)-5-oxopyrrolidine-2-carbonyl)-L-valine pentafluorophenyl ester
• CAS NO: 938075-92-4
• Molecular Weight: 494.415
• Mol File: 938075-92-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-((S)-1-(1,1-dimethylethoxycarbonyl)-5-oxopyrrolidine-2-carbonyl)-L-valine pentafluorophenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-((S)-1-(1,1-dimethylethoxycarbonyl)-5-oxopyrrolidine-2-carbonyl)-L-valine pentafluorophenyl ester(938075-92-4)
• EPA Substance Registry System: N-((S)-1-(1,1-dimethylethoxycarbonyl)-5-oxopyrrolidine-2-carbonyl)-L-valine pentafluorophenyl ester(938075-92-4)

Safety Data

• Hazardous Substances Data: 938075-92-4(Hazardous Substances Data)

Upstream product

• 98-79-3 L-Pyroglutamic acid 
• 94885-52-6 benzyl (L)-pyroglutamate 
• 53100-44-0 L-N-t-butoxycarbonylpyroglutamic acid 
• 113400-36-5 benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate 
• 21760-98-5 L-valine benzyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 938075-90-2 N-((S)-1-(1,1-dimethylethoxycarbonyl)-5-oxopyrrolidine-2-carbonyl)-L-valine phenylmethyl ester 
• 938075-91-3 N-((S)-1-(1,1-dimethylethoxycarbonyl)-5-oxopyrrolidine-2-carbonyl)-L-valine 
• 14533-84-7 pentafluorophenyl trifloroacetate 

Relevant articles and documents

Synthetic approaches to peptides containing the l-Gln-l-Val-D(S)-Dmt motif

The pseudoprolines S-Dmo (5,5-dimethyl-4-oxaproline) and R-Dmt (5,5-dimethyl-4-thiaproline) have been used to study the effects of forcing a fully cis conformation in peptides. Synthesis of peptides containing these (which have the same configuration as l-Pro) is straightforward. However, synthesis of peptides containing S-Dmt is difficult, owing to the rapid cyclisation of l-Aaa-S-Dmt amides and esters to form the corresponding diketopiperazines (DKP); thus the intermediacy of l-Aaa-S-Dmt amides and esters must be avoided in the synthetic sequence. Peptides containing the l-Gln-l-Val-D(S)-Dmt motif are particularly difficult, owing to the insolubility of coupling partners containing Gln. Introduction of Gln as N-Boc-pyroglutamate overcame the latter difficulty and the dipeptide active ester BocPygValOC6F5 coupled in good yield with S-DmtOH. BocPygVal-S- DmtNH(CH2)2C6H4NO2 was converted quantitatively to BocGlnVal-S-DmtNH(CH2)2C6H4NO2 with ammonia, demonstrating the utility of this approach. Two peptide derivatives (CbzSerLysLeuGlnVal-S-DmtNH(CH2)2C6H4NO2 and CbzSerSerLysLeuGlnVal-S- DmtNH(CH2)2C6H4NO2) were assembled, using these new methods of coupling a dipeptide acid active ester with S-DmtOH and introduction of Gln as Pyg, followed by conventional peptide couplings. The presence of the Val caused these peptides to be cleaved very slowly by prostate-specific antigen (PSA) at Leu ↓ Gln, rather than the expected Gln ↓ Val.