77614-16-5

Basic information

• Product Name: DERMORPHIN ACETATE
• Synonyms: DERMORPHIN ACETATE;L-Tyr-D-Ala-L-Phe-Gly-L-Tyr-L-Pro-L-Ser-NH2;Tyrosyl-alanyl-phenylalanyl-glycyl-tyrosyl-prolyl-serinamide;Dermorphin trifluoroacetate salt
• CAS NO: 77614-16-5
• Molecular Formula: C₄₀H₅₀N₈O₁₀
• Molecular Weight: 802.881
• Mol File: 77614-16-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: 157-159 °C
• Boiling Point: 1323.8°C at 760 mmHg
• Flash Point: 754.4°C
• Appearance: white to off-white/
• Density: 1.363g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.628
• Storage Temp.: ?20°C
• PKA: 9.83±0.15(Predicted)
• CAS DataBase Reference: DERMORPHIN ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: DERMORPHIN ACETATE(77614-16-5)
• EPA Substance Registry System: DERMORPHIN ACETATE(77614-16-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 77614-16-5(Hazardous Substances Data)

Usage

Uses

A mu-opioid receptor agonist

InChI:InChI=1/C40H50N8O10/c1-23(44-37(55)29(41)18-25-9-13-27(50)14-10-25)36(54)46-30(19-24-6-3-2-4-7-24)38(56)43-21-34(52)45-31(20-26-11-15-28(51)16-12-26)40(58)48-17-5-8-33(48)39(57)47-32(22-49)35(42)53/h2-4,6-7,9-16,23,29-33,49-51H,5,8,17-22,41H2,1H3,(H2,42,53)(H,43,56)(H,44,55)(H,45,52)(H,46,54)(H,47,57)/t23-,29+,30+,31+,32+,33+/m1/s1

Synthetic route

Z-Tyr-D-Ala-Phe-Gly-Tyr-Pro-Ser-NH2 → dermorphin (77614-16-5)

Conditions	Yield
With formic acid; palladium	80%

BOC-glycine (4530-20-5) + 1-(tert-butoxycarbonyl)-L-proline (15761-39-4) + O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3) + BOC-O-benzyl-L-serine (23680-31-1) + Boc-Phe-OH, Boc-D-Ala-OH → dermorphin (77614-16-5)

Conditions	Yield
Yield given. Multistep reaction;

N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + Fmoc-Pro-OH (71989-31-6) + N-Fmoc L-Phe (35661-40-6) + Fmoc-Ser(tBu)-OH (71989-33-8) + Fmoc-Tyr(tBu)-OH (71989-38-3) + N-(9-fluorenylmethoxycarbonyl)-D-alanine (35661-38-2, 35661-39-3, 79990-15-1) → dermorphin (77614-16-5)

Conditions	Yield
Stage #1: Fmoc-Ser(tBu)-OH With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one; N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: With piperidine In 1-methyl-pyrrolidin-2-one for 0.333333h; Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Pro-OH; N-Fmoc L-Phe; Fmoc-Tyr(tBu)-OH; N-(9-fluorenylmethoxycarbonyl)-D-alanine Further stages;

dermorphin (77614-16-5) + 4-nitrophenol acetate (830-03-5) → N-Acetyl-Tyr-D-Ala-Phe-Gly-Tyr-Pro-Ser-NH2 (86129-31-9)

Conditions	Yield
In N,N-dimethyl-formamide at 0℃; for 12h;	76%

dermorphin (77614-16-5) → 1-[2-[2-(2-{2-[2-amino-3-(4-hydroxy-3,5-diiodo-phenyl)-propionylamino]-propionylamino}-3-phenyl-propionylamino)-acetylamino]-3-(4-hydroxy-3,5-diiodo-phenyl)-propionyl]-pyrrolidine-2-carboxylic acid (1-carbamoyl-2-hydroxy-ethyl)-amide

Conditions	Yield
With [bis(pyridine)iodine]+ tetrafluoroborate In dichloromethane at 20℃; for 0.166667h; Iodination;

Upstream product

• 4530-20-5 BOC-glycine 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 2130-96-3 O-benzyl-N-tert-butoxycarbonyl-L-tyrosine 
• 23680-31-1 BOC-O-benzyl-L-serine 
• 29022-11-5 N-(fluoren-9-ylmethoxycarbonyl)glycine 
• 71989-31-6 Fmoc-Pro-OH 
• 35661-40-6 N-Fmoc L-Phe 
• 71989-33-8 Fmoc-Ser(tBu)-OH 
• 71989-38-3 Fmoc-Tyr(tBu)-OH 
• 35661-38-2 N-(9-fluorenylmethoxycarbonyl)-D-alanine 

Downstream Products

• 86129-31-9 N-Acetyl-Tyr-D-Ala-Phe-Gly-Tyr-Pro-Ser-NH₂ 

Relevant articles and documents

A Blocking Group Scan Using a Spherical Organometallic Complex Identifies an Unprecedented Binding Mode with Potent Activity In Vitro and In Vivo for the Opioid Peptide Dermorphin

Herein, the selective enforcement of one particular receptor-ligand interaction between specific domains of the μ-selective opioid peptide dermorphin and the μ opioid receptor is presented. For this, a blocking group scan is described which exploits the steric demand of a bis(quinolinylmethyl)amine rhenium(I) tricarbonyl complex conjugated to a number of different, strategically chosen positions of dermorphin. The prepared peptide conjugates lead to the discovery of two different binding modes: An expected N-terminal binding mode corresponds to the established view of opioid peptide binding, whereas an unexpected C-terminal binding mode is newly discovered. Surprisingly, both binding modes provide high affinity and agonistic activity at the μ opioid receptor in vitro. Furthermore, the unprecedented C-terminal binding mode shows potent dose-dependent antinociception in vivo. Finally, in silico docking studies support receptor activation by both dermorphin binding modes and suggest a biological relevance for dermorphin itself. Relevant ligand-protein interactions are similar for both binding modes, which is in line with previous protein mutation studies.

Structure-Activity Studies of Dermorphin. Synthesis and Some Pharmacological Data of Dermorphin and Its 1-Substiituted Analogues

Dermorphin and its analogues substituted at position 1 by N-acetyltyrosine, O-methyltyrosine, phenylalanine, D-phenylalanine, or alanine were obtained by solid-phase peptide synthesis.Their pharmacological effects were studied in vitro by the guinea pig ileum method and in vivo by the hot plate method, and the results were compared with those of morphine.The most pronounced activity was shown for dermorphin.A radioreceptor study showed a moderate affinity of dermorphin and its Tyr(Me)1 analogue for the opiate receptor sites from striatal homogenates.