L-Phenylalanine → (+)-Phenylahistin

HRID 1795016

Reaction equation

HRID 1795016 reaction equation
[CH3:1][C:2]([C:6]1[NH:10][CH:9]=[N:8][C:7]=1/[CH:11]=[C:12]1/[C:13]([NH:15][C@@H:16]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:17]([NH:19]/1)=[O:18])=[O:14])([CH:4]=[CH2:5])[CH3:3].N[C@H](C(O)=O)CC1C=CC=CC=1>CCCCCC.C(O)C>[CH3:3][C:2]([C:6]1[NH:10][CH:9]=[N:8][C:7]=1/[CH:11]=[C:12]1/[C:13]([NH:15][C@H:16]([CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:17]([NH:19]/1)=[O:18])=[O:14])([CH:4]=[CH2:5])[CH3:1]

Participants

4

Reactant 2

HCID 6140L-PhenylalanineHCID 9798496Phenylahistin

Product 1

HCID 44328528(+)-Phenylahistin

Reagents, catalysts & solvents 1

HCID 21879635Ethanol hexaneSolvent

Procedure

It was also determined that phenylahistin has a chiral center at the C-10 position. Chiral HPLC analysis of the phenylalanine was conducted according to methods described in Larsen, T. O et al., Phytochemistry (1992) 31, 1613, under the following conditions: HPLC conditions: column; Crownpak CR(+) N4.0×150 mm (Daicel Chemical Industries, Ltd.), mobile phase; H2O (pH 2, adjusted with perchloric acid), flow rate; 0.8 ml/min, detector; UV 8 200 nm. Phenylalanine was obtained from the acidic hydrolysate of the amorphous white powder of phenylahistin, see Yamazaki, M. et al., Tetrahedron Lett. (1975) 27. The phenylalanine obtained from the hydrolysate of phenylahistin was identified using an amino acid analyzer and by measurement of EI-MS [(m+H)+:166.2]); chrial HPLC indicated that the phenylahistin was a mixture of enantiomers in the ratio of approximately R:S=3.1. In order to examine the biological activity of each enantiomer, chiral resolution was carried out by chiral HPLC under the following conditions: column; Chiracel OD N4.6×250 mm (Daicel Chemical Industries, Ltd), mobile phase; n-hexane/ethanol=75/25, flow rate; 1.0 ml/min, temperature; 25° C. Absolute configuration was determined by analysis of phenylalanine obtained from (+)-phenylahistin using chiral HPLC.

Workup

  1. additiona mixture of enantiomers in the ratio of approximately R
  2. custom25° C

Sources & evidence

ORD record
ord-b8a9e409dae442d6827b608ff5aafa39
Source dataset
uspto-grants-2006_04
Patent number
US07026322B2

Linked notes

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