Indole → l-tryptophyl-D-alanine

HRID 1720570Notes

Reaction equation

HRID 1720570 reaction equation
N1C2C(=CC=CC=2)C=C1.[NH2:10][C@H:11]([C:13]([OH:15])=[O:14])[CH3:12].[NH2:16][C@H:17]([C:28](O)=[O:29])[CH2:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:21][CH:20]=1>>[NH2:16][C@H:17]([C:28]([NH:10][C@@H:11]([C:13]([OH:15])=[O:14])[CH3:12])=[O:29])[CH2:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:21][CH:20]=1

Participants

4

Reactant 3

HCID 798Indole5×HCID 5950L-Alanine2×HCID 6305L-Tryptophan5×

Product 1

HCID 61578895l-tryptophyl-D-alanine

Procedure

NMR (1H) in DMSO-d6 10.88 (1H, s) NH indole, 8.20 (1H, broad s) NH Ala, 7.58 (1H, d) H4 indole, 7.32 (1H, d) H7 indole, 7.16 (1H, s) H2 indole, 7.05 (1H, t) H6 indole, 6.97 (1H, t) H5 indole, 4.05 (1H, broad q) Hα Ala, 3.73 (1H, dd) Hα Trp, 3.12 (1H, dd) HβA Trp, 2.88 (1H, dd) HβB Trp, 1.12 (1H, t) CH3 Ala

Sources & evidence

ORD record
ord-a054c430cebd4b4db38ea5a975fb44a0
Source dataset
uspto-grants-1996_04
Patent number
US05506362

Reaction notes

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