Efficient syntheses of thiadiazole peptides.
Novel N-(Cbz-aminoacyl)thiosemicarbazides 3a-c were cyclized by treatment with sulfuric acid to give 1,3,4-thiadiazoles 4a-c. Compounds 4a-c reacted with N-(Cbz-aminoacyl)- and -dipeptidoylbenzotriazoles to afford chirally pure 1,3,4-thiadiazol-2-yl-substituted amino acids 6a-c and dipeptides 7a-c.
Katritzky
Alan R
AR
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, USA. katritzky@chem.ufl.edu
El-Nachef
Claudia
C
Bajaj
Kiran
K
Kubik
Jonathan
J
Haase
Danniebelle N
DN
D008968:Molecular Conformation; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013830:Thiadiazoles / Q000138:chemical synthesis* / Q000737:chemistry
D010455:Peptides; D013830:Thiadiazoles