HCID 54540940, compound → Glycine

HRID 329553Notes

Reaction equation

[CH:1]1C2C(COC(=O)CCC[NH:20][C@H:21]([C:24]([OH:26])=[O:25])CS)C3C(=CC=CC=3)C=2C=CC=1.C1C2C(COC(CS)[C@@H](C(O)=O)NCCC=O)C3C(=CC=CC=3)C=2C=CC=1.N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C([NH:108][C@H:109]([C:125]([O:127]CC1C=CC=CC=1)=[O:126])[CH2:110][C:111]1[CH:116]=[CH:115][C:114]([O:117]CC2C=CC=CC=2)=[CH:113][CH:112]=1)=O)CCCNC(=N)NS(C1C=CC(C)=CC=1)(=O)=O)=O)CC1C=CC=CC=1)=O)COCC1C=CC=CC=1)=O)CC(=O)N>>[NH2:20][CH2:21][C:24]([OH:26])=[O:25].[NH2:108][C@H:109]([C:125]([OH:127])=[O:126])[C@H:110]([CH2:111][CH3:116])[CH3:1].[NH2:108][C@H:109]([C:125]([OH:127])=[O:126])[CH2:110][C:111]1[CH:116]=[CH:115][CH:114]=[CH:113][CH:112]=1.[NH2:108][C@H:109]([C:125]([OH:127])=[O:126])[CH2:110][C:111]1[CH:112]=[CH:113][C:114]([OH:117])=[CH:115][CH:116]=1

Participants

Reactant 3

HCID 54540940HCID 54540940, compound

HCID 131716236HCID 131716236, compound

HCID 178427519HCID 178427519, compound

Product 4

HCID 750Glycine

HCID 6057L-Tyrosine

HCID 6140L-Phenylalanine

HCID 6306L-Isoleucine

Procedure

By following the procedure of Examples 5 to 12, but replacing N-(t-butyloxycarbonyl)-S-(4-(9-fluorenylmethoxy)-4-oxobutyl-L-cysteine with N-(t-butyloxycarbonyl)-S-(3-(9-fluorenylmethoxy)-3-oxopropyl-L-homocysteine, and replacing H-Asn-Ser(Bzl)-Phe-Arg(Tos)-Tyr(Bzl)-OCH3 with H-Asn-Ser(Bzl)-Phe-Arg(Tos)-Tyr(Bzl)-OBzl, rat[(CH2CH2CO)105, hCys121 ]ANF-(105-126) is obtained Amino acid analysis of the product (1,Q=CH2CH2, R1=Phe, R2 =Gly, R3 =Ile, R4 =Phe, R5 =Tyr, X=S, Y1 des-Y and W is hydroxy) gave Asn+Asp (2.00), Ser (1.78), Gln (1.01), Gly(5.18), Ala (1.00), Ile (1.80), Leu (1.02), Tyr (0.99), Phe (2.00), Arg (3.45). Molecular weight was determined by FAB mass spectroscopy: C102H156N32O30S requires 2342.6: found, 2342M+.

Sources & evidence

ORD record: ord-33b2579f79d141afb99e74d84d9d169b
Source dataset: uspto-grants-1990_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04891358

Reaction notes

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