Prevalence of eight-membered hydrogen-bonded rings in some bis(cyclobutane) beta-dipeptides including residues with trans stereochemistry.
Three new bis(cyclobutane) beta-dipeptides have been synthesized from appropriate derivatives of cis- and trans-2-aminocyclobutane-1-carboxylic acid, respectively. The predominance of eight-membered hydrogen-bonded rings has been manifested for (trans,trans)- and (trans,cis)-beta-dipeptides while the formation of six-membered rings is preferred for the (cis,trans)- beta-dipeptide similarly to the previously described (cis,cis)-diastereomer.
Torres
Elisabeth
E
Departament de Química, Universitat Autònoma de Barcelona, 08193 Bellaterra, Barcelona, Spain.
Gorrea
Esther
E
Da Silva
Eric
E
Nolis
Pau
P
Branchadell
Vicenç
V
Ortuño
Rosa M
RM
D000598:Amino Acids, Cyclic / Q000737:chemistry*; D003503:Cyclobutanes / Q000737:chemistry*; D004151:Dipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D006860:Hydrogen Bonding; D015394:Molecular Structure; D013237:Stereoisomerism
C541323:2-aminocyclobutane-1-carboxylic acid; D000598:Amino Acids, Cyclic; D003503:Cyclobutanes; D004151:Dipeptides