L-Aspartic Acid → L-Glutamine

HRID 1856832Notes

Reaction equation

HRID 1856832 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4](O)=O.N[C@@H](CCCC)[C:12]([OH:14])=O.[NH2:19][C@H](CCCCC)C(O)=O.N[C@H](CCCCCC)C(O)=O.NC(CCCCCC)C(O)=O>>[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH2:4][C:12](=[O:14])[NH2:19]

Participants

6

Reactant 5

HCID 5960L-Aspartic AcidHCID 21236CaprineHCID 695222-Aminooctanoic acidHCID 1615251(R)-2-AMINOOCTANOIC ACIDHCID 5312964(R)-2-Aminoheptanoic acid

Product 1

HCID 5961L-Glutamine

Procedure

In a similar manner using the dimethyl esters of (S)-aspartic acid, (S)-2-aminohexanoic acid, (R)-2-aminoheptanoic acid, (R)-2-aminooctanoic acid, (RS)-2-aminooctanoic acid, and the methyl ester of (S)-glutamine in place of (S)-glutamic acid dimethyl ester, there were obtained 2-[4-(2(R)-carboxypyrrolidine-1-sulfonyl)benzoylamino]butane-(S)-dioic acid, MS: calc. 414, obs. 415 (M+H), 2-[4-(2(R)-carboxypyrrolidine-1-sulfonyl)benzoylamino]hexane-(S)-dioic acid, MS: calc. 442, obs. 443 (M+H), 2-[4-(2(R)-carboxypyrrolidine-1-sulfonyl)benzoylamino]heptane-(S)-dioic acid, MS: calc. 456, obs. 457 (M+H), 2-[4-(2(R)-carboxypyrrolidine-1-sulfonyl)benzoylamino]octane-(R)-dioic acid, MS: calc. 470, obs. 471 (M+H), 2-[4-(2(R)-carboxypyrrolidine-1-sulfonyl)benzoylamino]octane-(RS)-dioic acid, MS: calc. 470, obs. 471 (M+H), and 4-aminocarbonyl-2-[4-(2(R)-carboxypyrrolidine-1-sulfonyl)benzoylamino]-(S)-butanoic acid, MS: calc. 427, obs. 428 (M+H).

Sources & evidence

ORD record
ord-0290e0a3ee0f49249bba8f7254f87976
Source dataset
uspto-grants-2000_11
Patent number
US06143776

Reaction notes

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