Seglitide

Base Information

• Chemical Name: Seglitide
• CAS No.: 81377-02-8
• Molecular Formula: C44H56 N8 O7
• Molecular Weight: 808.978
• UNII: 5P57R7IR6J
• Nikkaji Number: J410.751I
• Wikidata: Q27088775
• NCI Thesaurus Code: C152317
• ChEMBL ID: CHEMBL311695
• Mol file: 81377-02-8.mol

Synonyms:cyclo(MATTLVP);cyclo(N-Me-Ala-Tyr-Trp-Lys-Val-Phe);cyclo(N-methylalanyl-tyrosyl-tryptophyl-lysyl-valyl-phenylalanyl);L 363586;L-363586;MK 678;MK-678;seglitide;seglitide acetate;seglitide monoacetate

Chemical Property of Seglitide

Chemical Property:

• Boiling Point: 1194.3±65.0 °C(Predicted)
• PKA: pKa 9.7(H2O) (Uncertain)
• PSA: 227.85000
• Density: 1.186±0.06 g/cm3(Predicted)
• LogP: 4.25310
• Storage Temp.: 2-8°C
• Solubility.: H2O: 26 mg/mL, soluble
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 11
• Exact Mass: 808.42719616
• Heavy Atom Count: 59
• Complexity: 1430

Purity/Quality:

98%min ^*data from raw suppliers

Seglitide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1C)CC2=CC=CC=C2)C(C)C)CCCCN)CC3=CNC4=CC=CC=C43)CC5=CC=C(C=C5)O
• Isomeric SMILES: C[C@H]1C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1C)CC2=CC=CC=C2)C(C)C)CCCCN)CC3=CNC4=CC=CC=C43)CC5=CC=C(C=C5)O
• Uses: Antidiabetic. Seglitide is a somatostatin (SST) agonist.

Technology Process of Seglitide

There total 11 articles about Seglitide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 52.0%

N-Fmoc-Tyr-OH (112883-29-1,92954-90-0) + N-(9-fluorenylmethoxycarbonyl)-N-methyl-L-alanine (84000-07-7) + Fmoc-Lys-OH (105047-45-8) + N-(9-fluorenylmethoxycarbonyl)-D-tryptophan (35737-15-6,144701-22-4,86123-11-7) → MK-678 (81377-02-8)

Guidance literature:

Multistep reaction;

DOI:10.1016/S0040-4039(99)01701-3

Reference yield:

cyclo-(D-Trp-Lys(Cbz)-Val-Phe-N-Me-Ala-Tyr-) (86066-92-4) → MK-678 (81377-02-8)

Guidance literature:

With formic acid; palladium on activated charcoal; In methanol; for 2.5h; Yield given;

DOI:10.1021/jo00381a011

Reference yield:

Boc-L-Lys(Z)-OMe (73548-77-3) → MK-678 (81377-02-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 92.5 percent / N-methylmorpholine / CH₂Cl₂ / 2 h

2: 100 percent / 2.5 N NaOH, / tetrahydrofuran; H₂O / 6 h

3: N-methylmorpholine / ethyl acetate / 0.2 h / -5 °C

4: N-methylmorpholine / ethyl acetate; dimethylformamide / 1.5 h / -5 °C

5: 2.5 N NaOH / tetrahydrofuran; H₂O / 6 h

6: HCl(gas) / ethyl acetate / 0.75 h / 0 °C

7: 76.6 percent / diphenylphosphoryl azide (DPPA), NaHCO₃ / dimethylformamide / 72 h / 0 - 5 °C

8: HCOOH / 10percent Pd/C / methanol / 2.5 h

With 4-methyl-morpholine; hydrogenchloride; sodium hydroxide; formic acid; diphenylphosphoranyl azide; sodium hydrogencarbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo00381a011

upstream raw materials:

cyclo-(D-Trp-Lys(Cbz)-Val-Phe-N-Me-Ala-Tyr-)

N-Fmoc-Tyr-OH

N-(9-fluorenylmethoxycarbonyl)-N-methyl-L-alanine

Fmoc-Lys-OH

Refernces

• 1、 Brady,Freidinger,Paleveda,et al.. "Large-scale synthesis of a cell cyclic hexapeptide analogue of somatostatin". . p. 764 - 769. Retrieved 2007/10/02.