82146-10-9

Basic information

• Product Name: C₂₇H₃₂N₂O₇
• CAS NO: 82146-10-9
• Molecular Weight: 496.56
• Mol File: 82146-10-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: C₂₇H₃₂N₂O₇(CAS DataBase Reference)
• NIST Chemistry Reference: C₂₇H₃₂N₂O₇(82146-10-9)
• EPA Substance Registry System: C₂₇H₃₂N₂O₇(82146-10-9)

Safety Data

• Hazardous Substances Data: 82146-10-9(Hazardous Substances Data)

Upstream product

• 2448-45-5 N-(Benzyloxycarbonyl)-D-phenylalanine 
• 63358-25-8 Z-D-Phe-OTCP 
• 17460-56-9 Z-D-Phe-Pro 
• 543-27-1 isobutyl chloroformate 

Downstream Products

• 126644-60-8 N-[3-(5-Benzyl-6-oxo-5,6,8,9,10,10a-hexahydro-imidazo[1,2-a]pyrrolo[2,1-c]pyrazin-2-yl)-propyl]-guanidine 
• 83997-16-4 D-Phe-Pro-Arg-H*H₂SO₄ 
• 77433-27-3 Z-D-Phe-Pro-Arg(Z)-H 
• 61635-50-5 Z-D-Phe-Pro-Arg(Z)> 

Relevant articles and documents

Highly active and selective anticoagulants: D-Phe-Pro-Arg-H, a free tripeptide aldehyde prone to spontaneous inactivation, and its stable N-methyl derivative, D-MePhe-Pro-Arg-H

D-Phe-Pro-Arg-H sulfate (GYKI-14166) is a highly active and selective inhibitor of thrombin both in vitro and in vivo. Recent studies on the stability of D-Phe-Pro-Arg-H in neutral aqueous solution at higher temperature have revealed that it is transformed into inactive 5,6,8,9,10,10a-hexahydro-2-(3'-guanidinopropyl)-5-benzyl-6-oxo-imidazo [1,2-a]pyrrolo[2,1-c]pyrazine. No such inactivation could be observed with Boc-D-Phe-Pro-Arg-H (GYKI-14451), but this compound was far less specific than the free peptide as it inhibited thrombin and, for instance, plasmin equally well. Assuming that the transformation of free tripeptide aldehyde, mentioned above, can only be initiated by a primary amino terminus, the N-alkyl derivatives of D-Phe-Pro-Arg-H were prepared. Of the new analogues, D-MePhe-Pro-Arg-H (GYKI-14766) proved to be as highly active and selective anticoagulant as its parent compound and was not inactivated by transformation into a heterocyclic compound.