186043-94-7

Basic information

• Product Name: H-Asn(Mtt)-Pro-Asn(Mtt)-Ala-Ala Pro(NH₂)=Pro(CH₂COOH) Ala-OH
• CAS NO: 186043-94-7
• Molecular Weight: 1318.54
• Mol File: 186043-94-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: H-Asn(Mtt)-Pro-Asn(Mtt)-Ala-Ala Pro(NH₂)=Pro(CH₂COOH) Ala-OH(CAS DataBase Reference)
• NIST Chemistry Reference: H-Asn(Mtt)-Pro-Asn(Mtt)-Ala-Ala Pro(NH₂)=Pro(CH₂COOH) Ala-OH(186043-94-7)
• EPA Substance Registry System: H-Asn(Mtt)-Pro-Asn(Mtt)-Ala-Ala Pro(NH₂)=Pro(CH₂COOH) Ala-OH(186043-94-7)

Safety Data

• Hazardous Substances Data: 186043-94-7(Hazardous Substances Data)

Upstream product

• 51-35-4 4R-4-hydroxyproline 
• 13504-85-3 (2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 
• 186043-88-9 methyl (2S,4S)-1-[(2S,4R)-1-(benzyloxycarbonyl)-4-hydroxyprolyl]-4-phthalimidoprolinate 
• 186043-92-5 [(2R,5aS,7S,10aS)-7-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-5,10-dioxo-octahydro-dipyrrolo[1,2-a;1',2'-d]pyrazin-2-yl]-acetic acid methyl ester 
• 186043-91-4 [(5aS,7S,10aS)-7-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-5,10-dioxo-hexahydro-dipyrrolo[1,2-a;1',2'-d]pyrazin-(2Z)-ylidene]-acetic acid methyl ester 
• 186043-89-0 (2S,5aS,7R,10aS)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-7-hydroxy-octahydro-dipyrrolo[1,2-a;1',2'-d]pyrazine-5,10-dione 
• 186043-90-3 (5aS,7S,10aS)-7-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-hexahydro-dipyrrolo[1,2-a;1',2'-d]pyrazine-2,5,10-trione 
• 35661-39-3 N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine 
• 71989-31-6 Fmoc-Pro-OH 
• 200259-50-3 Fmoc-Asn(4-methyltrityl)-OH 
• 186043-93-6 [(2R,5aS,7S,10aS)-7-(9H-Fluoren-9-ylmethoxycarbonylamino)-5,10-dioxo-octahydro-dipyrrolo[1,2-a;1',2'-d]pyrazin-2-yl]-acetic acid 

Relevant articles and documents

A tricyclic template derived from (2S,4R)-4-hydroxyproline for the synthesis of protein loop mimetics

A tricyclic diketopiperazine, formally derived by coupling (2S,4S)-4-aminoproline (Pro(NH2)) and (2S,4R)-4-(carboxymethyl)proline (Pro(CH2COOH)), is synthesized starting from readily available (2S,4R)-4-hydroxyproline. The resulting tricyclic template has carboxy and amino groups to which a peptide chain may be attached. The Fmoc-protected template 5 is incorporated into the cyclic molecule cyclo(-Ala1-Asn2-Pro3-Asn4-Ala5-Ala6 Pro(NH2)7 = Pro(CH2COOH)8 ) (6) where Pro(NH2)7 = Pro(CH2COOH)8 represents the template, using solid-phase peptide synthesis with cyclization in solution. The molecule is shown by NMR and dynamic simulated annealing methods to adopt a preferred conformation in aqueous solution, which includes an extended backbone at the residues Asn2-Pro3-Asn4, and a type-Iβ-turn at Asn4-Ala5-Ala6 Pro(NH2)7. These studies show that this novel template may be used in the synthesis of cyclic peptide and protein mimetics having defined secondary structure in aqueous environments.