L-Leucine → HCID 46174011, compound

HRID 2371774Notes

Reaction equation

CC(C(N)C([NH:7][C@H:8]([C:16]([NH:18][C@H:19]([C:27]([OH:29])=[O:28])/[CH:20]=[CH:21]\[CH2:22][P:23]([OH:26])([OH:25])=[O:24])=[O:17])[CH2:9][CH2:10][CH2:11][N:12]=[C:13]([NH2:15])[NH2:14])=O)C.[NH2:31][C@H:32]([C:37]([OH:39])=O)[CH2:33][CH:34]([CH3:36])[CH3:35].N[C@H](C(O)=O)[C@H](CC)C>>[CH3:36][CH:34]([CH2:33][CH:32]([NH2:31])[C:37]([NH:7][C@H:8]([C:16]([NH:18][C@H:19]([C:27]([OH:29])=[O:28])/[CH:20]=[CH:21]\[CH2:22][P:23]([OH:25])([OH:26])=[O:24])=[O:17])[CH2:9][CH2:10][CH2:11][N:12]=[C:13]([NH2:14])[NH2:15])=[O:39])[CH3:35]

Participants

Reactant 3

HCID 6106L-Leucine

HCID 6306L-Isoleucine

HCID 46174006HCID 46174006, compound

Product 1

HCID 46174011HCID 46174011, compound

Procedure

After Sephadex G-10 purification isolates of rhizocticine B are microheterogeneous, that is to say 0.5%-5% of the N-terminal amino acid valine is replaced by leucine and by isoleucine. Small amounts of the likewise antifungal tripeptides rhizocticine C (L-Ile-L-Arg-L-APPA) and rhizocticine D (L-Leu-L-Arg-L-APPA) can be isolated from the mixture by means of HPLC.

Sources & evidence

ORD record: ord-964c581c57ca4798a62ae937ca9fcb96
Source dataset: uspto-grants-1992_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05095139

Reaction notes

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