Myristoyl Pentapeptide-4 CAS#: 1392416-25-9; ChemWhat Code: 1491149
Identification
| Product Name | Myristoyl Pentapeptide-4 |
| IUPAC Name | (2S)-2-[[(2S)-6-amino-2-[[(2S,3R)-2-[[(2S,3R)-2-[[(2S)-6-amino-2-(tetradecanoylamino)hexanoyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxybutanoyl]amino]hexanoyl]amino]-3-hydroxypropanoic acid |
| Molecular Structure |  |
| Synonyms | myristoyl pentapeptide-4 MYR-KTTKS COLLASYN 514KS PMA59A699X MYRISTOYL PENTAPEPTIDE-3 MYR-LYS-THR-THR-LYS-SER MYRISTOYL PENTAPEPTIDE-4 [INCI] HY-P5239 CS-0863822 Q27286632 (2S)-2-[[(2S)-6-amino-2-[[(2S,3R)-2-[[(2S,3R)-2-[[(2S)-6-amino-2-(tetradecanoylamino)hexanoyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxybutanoyl]amino]hexanoyl]amino]-3-hydroxypropanoic acid 1392416-25-9 |
| Molecular Formula | C37H71N7O10 |
| Molecular Weight | 774 |
| InChI | InChI=1S/C37H71N7O10/c1-4-5-6-7-8-9-10-11-12-13-14-21-30(48)40-27(19-15-17-22-38)34(50)43-32(26(3)47)36(52)44-31(25(2)46)35(51)41-28(20-16-18-23-39)33(49)42-29(24-45)37(53)54/h25-29,31-32,45-47H,4-24,38-39H2,1-3H3,(H,40,48)(H,41,51)(H,42,49)(H,43,50)(H,44,52)(H,53,54)/t25-,26-,27+,28+,29+,31+,32+/m1/s1 |
| InChI Key | XLELDISCQSKJES-IPPMYLEBSA-N |
| SMILES | CCCCCCCCCCCCCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CO)C(=O)O |
Physical Data
| Appearance | White to off-white powder |
Spectra
No data available
Route of Synthesis (ROS)
| Conditions | Yield |
| Stage #1: With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 24 – 32℃; for 5h; Stage #2: With piperidine In N,N-dimethyl-formamide for 0.25h; Further stages; Experimental Procedure 1 1-1. Resin Swelling General procedure: A solid-phase synthesis reactor equipped with a filtration membrane was used.Peptide synthesis having a carboxyl group (-COOH) at the end of the complex was used with 2-chlorotrityl chloride resin (Bead Tech, Korea),Peptide synthesis was terminated with a peptide bond (-CONH2) at the end of the complex using a link amide resin (GLS, China).Resin was swollen for 20 minutes using dichloromethane and dimethylformamide to prepare the preparation.1-2. Amino acid loadingSynthesis with chlorotrityl chloride resin involves loading the first amino acid into the resin.The resin was removed solvent through a filtration membrane under reduced pressure.3 to 5 equivalents of the amino acid in the resin was completely dissolved in DMF and added to chlorotrityl chloride resin,In consideration of density, diisopropylethylamine was added in an amount corresponding to 3-5 equivalents of chlorotrityl chloride resin.Thereafter, the reaction was performed at 24 ° C. to 32 ° C. for at least 5 hours using a reactor. 1-3. Resin Fmoc DeprotectionSynthesis using the chlorotrityl chloride resin or linkamide resin included a process of deprotection of Fluorenylmethyloxycarbonyl chloride (Fmoc).Resin Fmoc deprotection process removes solvent through the membrane under reduced pressure,After washing for 5 minutes with DMF added 20% (v / v) piperidine, and then again for 10 minutes. The reaction solution was removed by filtration under reduced pressure, and washed six more times for five minutes using DCM or DMF. 1-4. Fatty acid-amino acid complexes and fatty acid- oligopeptide complexes synthesis3 to 5 equivalents of the amino acid in the link amide resin was completely dissolved in DMF, and the solvent was removed to the link amide resin.As a coupling reagent, 2 M HOBt / DIC (hydroxybenzotriazole / diisopropylcarbodiimide) was added to the amino acid equivalent and the link amide resin amount.Then, the synthesis was carried out at 24 ~ 32 5 hours or more using a reactor.After the reaction was completed, the solvent was removed through a filtration membrane under reduced pressure,Washed six times with clean DMF five times.After washing, the amino acids were coupled in sequence in the same manner as the amino acid binding method.Thereafter, 3 equivalents of fatty acid was added to the resin in the state where the peptide was synthesized.2 M HOBt / DIC was added according to amino acid equivalent and resin amount.After using the reactor for 5 hours or more, it was reacted at a temperature of 24 ~ 32 . 1-5. CleavageAfter the reaction was completed, the solvent was removed through the filtration membrane under reduced pressure twice with clean DMF twice for 2 minutes,After washing twice with DCM twice, the solvent was almost removed through the filtration membrane under reduced pressure.The dried peptide complex resin was separated for 4 hours using 70% (v / v) TFA / 29% (v / v) DCM / 1% (v / v) H2O solution.1-6. CrystallizeThe separated solvent was extracted by recrystallization of the crude product using ethyl ether. |
Safety and Hazards
| Precautionary Statement Codes | Not Classified |
Source: European Chemicals Agency (ECHA)
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Record Name: (1-Cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate
URL: https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/213446
Description: The information provided here is aggregated from the “Notified classification and labelling” from ECHA’s C&L Inventory. Read more: https://echa.europa.eu/information-on-chemicals/cl-inventory-database
Other Data
| Transportation | Store at -20°C to 8°C for long time, in container tightly sealed; Protect from light and moisture, in dry place |
| HS Code | |
| Storage | Store at -20°C to 8°C for long time, in container tightly sealed; Protect from light and moisture, in dry place |
| Shelf Life | 2 years |
| Market Price |
| Druglikeness | |
| Lipinski rules component | |
| Molecular Weight | 774.012 |
| logP | 0.03 |
| HBA | 17 |
| HBD | 11 |
| Matching Lipinski Rules | 1 |
| Veber rules component | |
| Polar Surface Area (PSA) | 295.53 |
| Rotatable Bond (RotB) | 38 |
| Matching Veber Rules | 0 |
| Toxicity/Safety Pharmacology |
| Quantitative Results |
| Use Pattern |
| Myristoyl Pentapeptide-4 CAS 1392416-25-9 is a fatty acid-modified pentapeptide compound primarily used in cosmetics and skincare products. |
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