647847-98-1

Upstream product

• 647847-95-8 (2S)-benzyl 2-(N-(9-fluorenylmethoxycarbonyl)amino)-4-hydroxybutanoate 
• 172525-85-8 N^α-(Fluoren-9-ylmethoxycarbonyl)-L-homoserine 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 593-56-6 N-methoxylamine hydrochloride 
• 511546-75-1 benzyl 2-fluorenylmethyloxycarbonyl-3-formylpropanoate 

Downstream Products

• 647848-02-0 benzyl N^α-fluorenylmethyloxycarbonyl-N^γ-tert-butyloxycarbonyl-N^γ-methoxy-α,γ-diamino-L-butanoate 
• 647848-00-8 benzyl N^α-fluorenylmethyloxycarbonyl-N^γ-methoxy-α,γ-diamino-L-butanoate 

Relevant academic research and scientific papers

Opioid peptides: synthesis and biological properties of [(N gamma-glucosyl,N gamma-methoxy)-alpha, gamma-diamino-(S)-butanoyl]4-deltorphin-1-neoglycopeptide and related analogues.

The [D-Ala2]deltorphin 1 sequence in which the aspartic acid residue is replaced by the N gamma-OCH3-alpha, gamma-diamino (S) butanoyl residue was synthesized using the Fmoc-chemistry-based solid phase procedure. The resulting deltorphin analogue was chemoselectively glucosylated by reaction with unprotected D-glucose (Glc). The Asn4-, (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-galactopyranosyl)-Asn4- and the (2-acetamido-2-deoxy-D-galactopyranosyl)-Asn4-deltorphin I were also prepared for comparison. The affinity of the new compounds for the delta-opioid receptor was expressed by the inhibition constant (Ki) of the binding of the delta-receptor selective ligand [3H]naltrindole (NTI) to rat brain membrane preparations. The in vitro biological activity of the synthetic peptides was compared with that of the mu-opioid receptor agonist dermorphin in guinea pig ileum (GPI) preparations and with that of the delta-opioid receptor agonist deltorphin I in mouse vas deferens (MVD) preparations. The substitution of Asp4 with Asn failed to affect drastically the Ki and IC50 values for delta-sites, suggesting that an electrostatic interaction does not play an essential role in the binding to delta-opioid sites. The steric hindrance of the side chain of the residue in position 4 affects binding to delta-sites. The increase of the Ki value is smaller when the sugar-peptide linkage involves the gamma-nitrogen of the Dab residue in comparison with the Asn amide side chain.