Cyclo(-Arg-Gly-Asp-D-Phe-Cys)

Base Information

• Chemical Name: Cyclo(-Arg-Gly-Asp-D-Phe-Cys)
• CAS No.: 862772-11-0
• Molecular Formula: C24H34N8O7S
• Molecular Weight: 578.649
• Mol file: 862772-11-0.mol

Synonyms:Cyclo(-Arg-Gly-Asp-D-Phe-Cys);Cyclo(-RGDfC), avb3 Integrin Binding Cyclic RGD Peptide;Cyclo(-RGDfC), avb3 Integrin Binding Cyclic RGD Peptide, c(RGDfC);Cyclo(-Arg-Gly-Asp-D-Phe-Cys) Acetate salt;c(RGDfC),cyclo(Arg-Gly-Asp-d-Phe-Cys)

Chemical Property of Cyclo(-Arg-Gly-Asp-D-Phe-Cys)

Chemical Property:

• PKA: 4.01±0.10(Predicted)
• PSA: 283.50000
• Density: 1.55±0.1 g/cm3(Predicted)
• LogP: -0.19920

Purity/Quality:

Cyclo(RGDfC) >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Cyclo(L-arginylglycyl-L-α-aspartyl-D-phenylalanyl-L-cysteinyl) is a peptide molecule which can be conjugated with hyperbranched amphiphilic block copolymer for cancer-targeted drug delivery and non-invasive positron emission tomography (PET) imaging in tumor-bearing mice.

Technology Process of Cyclo(-Arg-Gly-Asp-D-Phe-Cys)

There total 3 articles about Cyclo(-Arg-Gly-Asp-D-Phe-Cys) 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: 32.0%

Fmoc-Asp(OAll)-Pol + N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine (103213-32-7,167015-11-4) + Fmoc-D-Phe-OH (86123-10-6) + Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine (187618-60-6) → (arginine-glycine-aspartic acid-D-phenylalanine-cysteine) peptide (862772-11-0)

Guidance literature:

Fmoc-Asp(OAll)-Pol;

N-(fluoren-9-ylmethoxycarbonyl)glycine;

N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine; Fmoc-D-Phe-OH; Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine; Further stages;

DOI:10.1002/cbic.201000386

Reference yield:

N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + C22H20NO2PolS + Fmoc-D-Phe-OH (86123-10-6) → (arginine-glycine-aspartic acid-D-phenylalanine-cysteine) peptide (862772-11-0)

Guidance literature:

C₂₂H₂₀NO₂PolS; Fmoc-D-Phe-OH; With ethyl cyanoglyoxylate-2-oxime potassium; diisopropyl-carbodiimide; In N,N-dimethyl-formamide; for 1.5h; 2-chlorotritylchloride resin

With piperidine; In N,N-dimethyl-formamide; at 20 ℃; for 0.25h; 2-chlorotritylchloride resin

N-(fluoren-9-ylmethoxycarbonyl)glycine; protected Fmoc-Asp; protected Fmoc-Arg;

DOI:10.1002/ejoc.201300777

Reference yield:

C28H44N10O9S2 + mesna (19767-45-4) → (arginine-glycine-aspartic acid-D-phenylalanine-cysteine) peptide (862772-11-0)

Guidance literature:

With sodium dihydrogenphosphate; tris(2-carboxyethyl)phosphine; In aq. buffer; at 50 ℃; for 72h; pH=5.6;

DOI:10.1021/jacs.6b13271

upstream raw materials:

N-(fluoren-9-ylmethoxycarbonyl)glycine

N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine

Fmoc-D-Phe-OH

Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine

Downstream raw materials:

C₆₇H₉₀N₁₀O₁₆S₂

C₁₁₁H₁₅₅N₂₃O₂₈S₃