D-Tryptophan → Picolinic acid

HRID 374559Notes

Reaction equation

HRID 374559 reaction equation
N[C@@H](C(O)=O)CC1C=NC=CC=1.C1C=C[C:16]2NC=[C:19]([CH2:22][C@@H:23]([NH2:27])[C:24]([OH:26])=[O:25])[C:17]=2C=1.N[C@@H](C(O)=O)CC1C=C2C(C=CC=C2)=CC=1.NCCC1N=CNC=1>>[N:27]1[CH:16]=[CH:17][CH:19]=[CH:22][C:23]=1[C:24]([OH:26])=[O:25]

Participants

5

Reactant 4

HCID 9060D-Tryptophan2×HCID 12681443-(3-Pyridyl)-D-alanine2×HCID 2733661D-3-(2-Naphthyl)alanine2×HCID 178419017HCID 178419017, compound

Product 1

HCID 1018Picolinic acid

Procedure

D-PicLys was substituted by D-3Pal, D-Trp, D-PzcLys, D-2-Nal and D-NicLys. Peptides 7 and 10 with D-3-Pal and D-2-Nal, respectively, were inactive at 0.25 μg. D-Trp is neutral and D-PzcLys is less basic than D-PicLys. These amino acids might be a good choice for lowering histamine release. Analog 11 with D-NicLys showed 67% AOA/0.25 μg which confirms past results that picolinic acid is superior to nicotinic acid for acylation of lysine.

Sources & evidence

ORD record
ord-da29337fc6644ac597eaa5cc00ae9660
Source dataset
uspto-grants-1996_01
Patent number
US05480969

Reaction notes

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