L-(+)-Cysteine → L-Phenylalanine

HRID 1955959Notes

Reaction equation

[NH2:1][C@H:2]([C:5]([OH:7])=[O:6])[CH2:3]S.[NH2:8][C@H:9]([C:15]([OH:17])=[O:16])[CH2:10][CH2:11][C:12](=O)O.N[C@H:19]([C:24](O)=O)[CH2:20][CH2:21][CH2:22]N.[NH2:27][C@H:28]([C:34]([OH:36])=[O:35])[CH2:29][CH2:30][CH2:31]CN>>[NH2:1][C@@H:2]([C:5]([OH:7])=[O:6])[CH2:3][C:9]1[CH:15]=[C:22]2[C:12]([CH:24]=[CH:19][CH:20]=[CH:21]2)=[CH:11][CH:10]=1.[NH2:27][C@@H:28]([C:34]([OH:36])=[O:35])[CH2:29][CH:30]([CH3:31])[CH3:2].[NH2:8][C@H:9]([C:15]([OH:17])=[O:16])[CH2:10][C:11]1[CH:21]=[CH:20][CH:19]=[CH:24][CH:12]=1

Participants

Reactant 4

HCID 5862L-(+)-Cysteine

HCID 5962L-Lysine

HCID 6262L-(-)-Ornithine

HCID 33032L-Glutamic Acid

Product 3

HCID 6140L-Phenylalanine

HCID 439524D-Leucine

HCID 2733661D-3-(2-Naphthyl)alanine

Procedure

Yet another preferred group of antagonists has the following formula (including nontoxic salts thereof): (cyclo 30-33)Y-Asp-Leu-Thr-D-Phe-His-R14 -Leu-Arg-Glu-R18 -Leu-R20 -Nle-R22 -R23 -R24 -R25 -Gln-R27 -R28 -R29 -R30 -R31 -R32 -R33 -R34 -Arg-R36 -R37 -Nle-R39 -R40 -R41 -NH2 wherein Y is Ac, Acr or For; R14 is Leu or CML; R18 is Val, CML or Nle; R20 is Glu or D-Glu; R22 is Ala, Aib, D-Ala or Thr; R23 is Arg or Lys; R24 is Ala or Aib; R25 is Asp or Glu; R27 is Leu or CML; R28 is Ala or Aib; R29 is Gln or Glu; R30 is Glu or Cys; R31 is Ala or Aib; R32 is His, D-His, D-Arg, imBzlD-His, D-Nal, D-Glu, D-Ala, D-Pal, D-Trp, D-Dpr(Nic), D-Aph, D-Agl(Nic), D-Orn, D-Dbu, D-Dpr or D-Orn(Nic); R33 is Lys, Cys or Orn; R34 is Asn or Aib; R36 is Lys, CML or Leu; R37 is Leu or CML; R39 is Glu or Asp; R40 is Ile, CML, Aib or Glu; and R41 is Ile, Aib, CML or Ala; provided that when R30 is Cys, R33 is Cys; and when R30 is Glu, R33 is Orn or Lys; and provided further that D-2Nal or D-Leu or Phe may be substituted for D-Phe.

Sources & evidence

ORD record: ord-2c7f632b08d64004b49dde30a235251b
Source dataset: uspto-grants-1998_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05777073

Reaction notes

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