Glycine → L-Isoleucine

HRID 1598925Notes

Reaction equation

HRID 1598925 reaction equation
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].CC(N=C=N[CH:12]([CH3:14])[CH3:13])C.[CH3:15]N(C=O)C>CN(C1C=CN=CC=1)C>[NH2:1][C@H:2]([C:3]([OH:5])=[O:4])[C@H:14]([CH2:12][CH3:13])[CH3:15]

Participants

5

Reactant 3

HCID 750GlycineHCID 6228DimethylformamideHCID 12734Diisopropylcarbodiimide

Product 1

HCID 6306L-Isoleucine

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

The incorporation of the first amino acid, in this case glycine, implies the formation of an ester-type link between the handle and the Fmoc Gly derivative. For this kind of incorporation the resin is reacted with 4.1 g (5 equivalents) of Fmoc Gly in the presence of 168 mg (0.5 equivalents) of DMAP and 2.094 ml (5 equivalents) of DIPCDI in DMF for 90". Once the reaction is complete the resin is washed five times with DMF. An amino acid analysis or an acid hydrolysis of the resin gives the ratio of the Ile amino acid (internal standard) and the first amino acid Gly. In this way the real functionalization of the resin is known, normally varying between 0.35-0.69 mmol/g.

Workup

  1. washis washed five times with DMF
  2. customAn amino acid analysis or an acid hydrolysis of the resin

Sources & evidence

ORD record
ord-33254329cc8a46669967f4889255ac24
Source dataset
uspto-grants-1998_04
Patent number
US05739272

Reaction notes

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