Stereoselective synthesis of Psi[CH(2)O] pseudodipeptides and conformational analysis of a PhePsi[CH(2)O]Ala containing analogue of the drug desmopressin.
A method for synthesis of XaaPsi[CH(2)O]Ala/Gly pseudodipeptides in good yields and excellent diastereoselectivity from azido alcohols and (R)-2-chloropropionic acid or tert-butyl bromoacetate has been developed. Insertion of one of the pseudodipeptide building blocks in the peptide drug desmopressin revealed that methylene ether isosteres may have only a minor influence on the secondary structure of peptides.
Hedenström
Mattias
M
Organic Chemistry, Department of Chemistry, Umeå University, SE-901 87, Umeå, Sweden.
Holm
Lotta
L
Yuan
ZhongQing
Z
Emtenäs
Hans
H
Kihlberg
Jan
J
D024043:Collagen Type II / Q000031:analogs & derivatives; D003894:Deamino Arginine Vasopressin / Q000031:analogs & derivatives*; D004151:Dipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D004987:Ethers / Q000737:chemistry; D006490:Hemostatics / Q000737:chemistry; D008968:Molecular Conformation; D018716:Molecular Mimicry; D013237:Stereoisomerism
D024043:Collagen Type II; D004151:Dipeptides; D004987:Ethers; D006490:Hemostatics; D003894:Deamino Arginine Vasopressin