HCID 6923821、化合物 → Methyl alpha-methyl-D-tryptophanate

HRID 2396427

反応式

HRID 2396427 の反応式
[CH3:1][O:2][C:3](=[O:17])[C@:4]([CH3:16])([CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1)[NH2:5]>P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+]>[CH3:1][O:2][C:3](=[O:17])[C@@:4]([CH3:16])([CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1)[NH2:5]

参加物

3

反応物 1

HCID 6923821HCID 6923821、化合物

生成物 1

HCID 6923819Methyl alpha-methyl-D-tryptophanate収率 10,402.5%

試薬・触媒・溶媒 1

HCID 24243Trisodium Phosphate溶媒

実験手順

To a suspension of (±)-α-methyltryptophan methyl ester (150.0 mg, 0.646 mmol) in 50 mL of 50 mM sodium phosphate buffer pH 7.5 was added carboxypeptidase Y from Bakers Yeast (6.4 mg). The resulting suspension was stirred at ambient temperature. After 4 h, 75% conversion was observed by HPLC (C18 column, 254 nm detection, acid tR =9.0 min and ester tR =11.9 min). The reaction was extracted with 2×25 mL chloroform. The combined extracts were treated with brine, dried with magnesium sulfate, then concentrated in vacuo to yield (R)-α-methyltryptophan methyl ester (15.6 mg, 67.2 mmol, 10.4%). A portion of this α-methyl amino ester was derivatized with 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate (TAGIT). HPLC analysis of the resulting thioureas showed the (R,S)-diastereomer to be in >99% diastereomeric excess (C18 column, 254 nm detection, S,S)-diastereomer tR =15.9 min and (R,S)-diastereomer tR =16.8 min).

後処理

  1. additionwas added carboxypeptidase Y from Bakers Yeast (6.4 mg)
  2. extractionThe reaction was extracted with 2×25 mL chloroform
  3. additionThe combined extracts were treated with brine
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-9c71beaed8264b348facb4cab7b20ba6
出典データセット
uspto-grants-1996_02
特許番号
US05492830

関連ノート

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