148529-00-4

Basic information

• Product Name: Boc-Orn(Boc)-Phe-Phe-Gly-Leu-Nva(5-OBzl)-NH₂
• Synonyms: Boc-Orn(Boc)-Phe-Phe-Gly-Leu-Nva(5-OBzl)-NH₂
• CAS NO: 148529-00-4
• Molecular Weight: 1001.23
• Mol File: 148529-00-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Boc-Orn(Boc)-Phe-Phe-Gly-Leu-Nva(5-OBzl)-NH₂(CAS DataBase Reference)
• NIST Chemistry Reference: Boc-Orn(Boc)-Phe-Phe-Gly-Leu-Nva(5-OBzl)-NH₂(148529-00-4)
• EPA Substance Registry System: Boc-Orn(Boc)-Phe-Phe-Gly-Leu-Nva(5-OBzl)-NH₂(148529-00-4)

Safety Data

• Hazardous Substances Data: 148529-00-4(Hazardous Substances Data)

Upstream product

• 23234-83-5 Z(OMe)-Leu-OH 
• 102979-60-2 Boc-Orn(Boc)-Phe-Phe-Gly-OH 
• 148528-91-0 [(S)-1-((S)-4-Benzyloxy-1-carbamoyl-butylcarbamoyl)-3-methyl-butyl]-carbamic acid 4-methoxy-benzyl ester 
• 148528-88-5 Boc-Nva(5-OBzl)-NH₂ 
• 148529-07-1 (S)-5-Benzyloxy-2-tert-butoxycarbonylamino-pentanoic acid 

Relevant articles and documents

Synthesis of an analogue of the substance P C-terminal hexapeptide with modification at the glutaminyl and methioninyl residues and increased activity in NK-2 receptor type: Structure-activity relationships

Analogues of [Orn6]-SP6-11 have been synthesized in which the Met11 residue is replaced by Hse(CH3), Hse(Bzl), Nva(5-OCH3), Nva(5-OBzl) and Abu. These analogues were tested in 3 in vitro preparations representative of NK-1, NK-2 and NK-3 receptor types. The Hse(Bzl) analogue is 16.6-fold more potent than the parent hexapeptide at the NK-2 receptor and 2.4-fold more potent at the NK-3 receptor. The Nva(5-OCH3) analogue showed weak antagonist activity in NK-2 and NK-3 receptor types, being a full agonist at NK-1. It is concluded from structure-activity correlations that the role of Met11 side chain in substance P is associated with activity and/or efficacy, as appropriate modifications in the side chain may result either in agonists with increased activity compared to the parent hexapeptide or selective agonists or may induce antagonism.