Cyclo(-RGDfK)

Base Information

• Chemical Name: Cyclo(-RGDfK)
• CAS No.: 161552-03-0
• Molecular Formula: C27H41N9O7
• Molecular Weight: 603.679
• DSSTox Substance ID: DTXSID30436575
• Nikkaji Number: J870.734K
• ChEMBL ID: CHEMBL2332367
• Mol file: 161552-03-0.mol

Synonyms:Cyclo(-RGDfK);161552-03-0;Cyclo (-RGDfK);2-[(2S,5R,8S,11S)-8-(4-aminobutyl)-5-benzyl-11-[3-(diaminomethylideneamino)propyl]-3,6,9,12,15-pentaoxo-1,4,7,10,13-pentazacyclopentadec-2-yl]acetic acid;CHEMBL2332367;cyclo-(Arg-Gly-Asp-D-Phe-Lys);cyclo(Arg-Gly-Asp-DPhe-Lys);cyclo[Arg-Gly-Asp-d-Phe-Lys];cyclo(Arg-Gly-Asp-D-Phe-Lys);cyclo-[Arg-Gly-Asp-d-Phe-Lys];Cyclo(RGDfK);cyclo-rgdfk;SCHEMBL7743533;SCHEMBL17364341;DTXSID30436575;Cyclo(Arg-Gly-Asp-D-Phe-Lys-);NVHPXYIRNJFKTE-HAGHYFMRSA-N;EX-A4060;HY-P0023;BDBM50429459;CS-4203;MS-30644;A918886;2-((2S,5R,8S,11S)-8-(4-aminobutyl)-5-benzyl-11-(3-guanidinopropyl)-3,6,9,12,15-pentaoxo-1,4,7,10,13-pentaazacyclopentadecan-2-yl)acetic acid

Chemical Property of Cyclo(-RGDfK)

Chemical Property:

• Melting Point: 191℃ (decomposition)
• PKA: 4.01±0.10(Predicted)
• PSA: 288.17000
• Density: 1.47±0.1 g/cm3(Predicted)
• LogP: 0.43580
• Solubility.: ≥30.19 mg/mL in DMSO; insoluble in EtOH; ≥59.2 mg/mL in H2O
• XLogP3: -4.7
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 12
• Exact Mass: 603.31289468
• Heavy Atom Count: 43
• Complexity: 1010

Purity/Quality:

99% ^*data from raw suppliers

Cyclo ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1)CCCN=C(N)N)CCCCN)CC2=CC=CC=C2)CC(=O)O
• Isomeric SMILES: C1C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)CCCN=C(N)N)CCCCN)CC2=CC=CC=C2)CC(=O)O

Technology Process of Cyclo(-RGDfK)

There total 31 articles about Cyclo(-RGDfK) 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: 100.0%

C42H51ClN10O11 → [(2S,5R,8S,11S)-8-(4-Amino-butyl)-5-benzyl-11-(3-guanidino-propyl)-3,6,9,12,15-pentaoxo-1,4,7,10,13-pentaaza-cyclopentadec-2-yl]-acetic acid (161552-03-0)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; acetic acid; at 20 ℃; for 18h;

DOI:10.1039/c6ob02391f

Reference yield: 43.0%

H-Gly-(2-Cl)-Trt-pol + Fmoc-dPhe-OH + Fmoc-(tBu)Asp-OH (71989-14-5) + Nα-Fmoc-Nε-Trt-Lys (111061-54-2) + Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine (187618-60-6) → [(2S,5R,8S,11S)-8-(4-Amino-butyl)-5-benzyl-11-(3-guanidino-propyl)-3,6,9,12,15-pentaoxo-1,4,7,10,13-pentaaza-cyclopentadec-2-yl]-acetic acid (161552-03-0)

Guidance literature:

H-Gly-(2-Cl)-Trt-pol; Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine; With N-ethyl-N,N-diisopropylamine; [ethyl cyano(hydroxyimino)?acetato-O²]?tri-?1-?pyrrolidinylphosphonium hexafluorophosphate; at 20 ℃; for 1h; 2-CT Cl resin

With piperidine; In N,N-dimethyl-formamide; at 20 ℃; for 0.1h;

Fmoc-dPhe-OH; Fmoc-(tBu)Asp-OH; N^α-Fmoc-N^ε-Trt-Lys; Further stages;

DOI:10.1002/anie.201700446

Reference yield: 43.0%

H-Gly-(2-Cl)-Trt-pol + Fmoc-dPhe-OH + Fmoc-(tBu)Asp-OH (71989-14-5) + Fmoc-Lys(OAc)-OH (159766-56-0) + Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine (187618-60-6) → [(2S,5R,8S,11S)-8-(4-Amino-butyl)-5-benzyl-11-(3-guanidino-propyl)-3,6,9,12,15-pentaoxo-1,4,7,10,13-pentaaza-cyclopentadec-2-yl]-acetic acid (161552-03-0)

Guidance literature:

H-Gly-(2-Cl)-Trt-pol; Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine; With N-ethyl-N,N-diisopropylamine; [ethyl cyano(hydroxyimino)?acetato-O²]?tri-?1-?pyrrolidinylphosphonium hexafluorophosphate; at 20 ℃; for 1h; 2-CT Cl resin

With piperidine; In N,N-dimethyl-formamide; at 20 ℃; for 0.1h;

Fmoc-dPhe-OH; Fmoc-(tBu)Asp-OH; Fmoc-Lys(OAc)-OH; Further stages;

DOI:10.1002/anie.201700446

upstream raw materials:

C₄₅H₆₇N₉O₁₀S

Fmoc-(tBu)Asp-OH

Fmoc-D-Phe-OH

Alloc-L-Lys(N-Fmoc)-OH

Downstream raw materials:

C₇₃H₁₁₁N₂₃O₂₂

C₃₅H₄₅N₉O₉

C₅₁H₇₇N₁₁O₁₆S

[(2S,5R,8S,11S)-8-[4-((S)-2-Amino-3-hydroxy-propionylamino)-butyl]-5-benzyl-11-(3-guanidino-propyl)-3,6,9,12,15-pentaoxo-1,4,7,10,13-pentaaza-cyclopentadec-2-yl]-acetic acid

Refernces

• 1、 Wang, Weiping,Liu, Qian,Zhan, Changyou,Barhoumi, Aoune,Yang, Tianshe,Wylie, Ryan G.,Armstrong, Patrick A.,Kohane, Daniel S.. "Efficient Triplet-Triplet Annihilation-Based Upconversion for Nanoparticle Phototargeting". . p. 6332 - 6338. Retrieved 2015.
• 2、 Liu, Junjie,Cheng, Xiaozhong,Tian, Xiaobo,Guan, Dongliang,Ao, Jiwei,Wu, Zhimeng,Huang, Wei,Le, Zhiping. "Design and synthesis of novel dual-cyclic RGD peptides for αvβ3 integrin targeting". . p. 896 - 900. Retrieved 2019.
• 3、 López Rivas, Paula,Ran?elovi?, Ivan,Raposo Moreira Dias, André,Pina, Arianna,Arosio, Daniela,Tóvári, József,Mez?, Gábor,Dal Corso, Alberto,Pignataro, Luca,Gennari, Cesare. "Synthesis and Biological Evaluation of Paclitaxel Conjugates Involving Linkers Cleavable by Lysosomal Enzymes and αVβ3-Integrin Ligands for Tumor Targeting". . p. 2902 - 2909. Retrieved 2018/06/27.