Ninhydrin → HCID 178418600, compound

HRID 1602041Notes

Reaction equation

HRID 1602041 reaction equation
Cl.C(OC([NH:9][C@H:10]([C:18]([OH:20])=[O:19])[CH2:11][CH2:12][CH2:13][NH:14][C:15](=[NH:17])[NH2:16])=O)CCC.Cl.C(N=C=NCCCN(C)C)C.ON1C(=O)CCC1=O.C(Cl)(Cl)Cl.CO.[H][H].C1C=C2C(C(O)(O)C(=O)C2=CC=1)=O>C(Cl)(Cl)Cl>[NH2:9][C@H:10]([C:18]([OH:20])=[O:19])[CH2:11][CH2:12][CH2:13][NH:14][C:15](=[NH:16])[NH2:17]

Participants

7

Reactant 5

HCID 10236NinhydrinHCID 80170N-HydroxysuccinimideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178454194HCID 178454194, compoundHCID 178496759HCID 178496759, compound

Product 1

HCID 178418600HCID 178418600, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

75 mg (0.101 mmol) of dioleoylphosphatidylethanolamine (Avanti Polar Lipids, USA) (DOPE), 34.3 mg (0.110 mmol) of Nalpha -tret-butoxycarbonyl-arginine hydrochloride (Sigma, USA), 24.8 mg (0.129 mmol) of N-ethyl-N'-dimethylaminopropyl-carbodiimide hydrochloride (Sigma, USA), and 14.9 mg (0.129 mmol) of N-hydroxysuccinimide (Sigma, UAS) were dissolved in 2 ml of chloroform and incubated with agitation at 37° C. for 3 hours. At that point, TLC (CHCl3 --CH3OH--H2 65:25:4, silica) showed 100% conversion of DOPE (Rf 0.49) into faster moving, ninhydrin-negative product (Rf 0.69), identified as N-(Nalpha -tret-butoxycarbonyl-arginyl)-DOPE. This product was purified by chromatography on silica and deprotected by treatment with 4M HCl in anhydrous dioxane for 3 hours. After removal of volatiles in vacuum, the residue was chromatographed on silica, eluent CHCl3 --CH3OH 7:3, to obtain Arg-PE (Rf 0.26 in the above system) with the yield of 10.8 mg (12% of theory). Phosphate to primary amino group ratio: Theory 1.0, Found 0.90±0.12.

Workup

  1. customThis product was purified by chromatography on silica and deprotected by treatment with 4M HCl in anhydrous dioxane for 3 hours
  2. customAfter removal of volatiles in vacuum
  3. customthe residue was chromatographed on silica, eluent CHCl3 --CH3OH 7:3

Sources & evidence

ORD record
ord-088669c37b6c4e9ba43f0b516eee7fa1
Source dataset
uspto-grants-1999_11
Patent number
US05980935

Reaction notes

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