TY - JOUR
T1 - A capped dipeptide which simultaneously exhibits gelation and crystallization behavior
AU - Martin, Adam D.
AU - Wojciechowski, Jonathan P.
AU - Bhadbhade, Mohan M.
AU - Thordarson, Pall
PY - 2016/3/8
Y1 - 2016/3/8
N2 - Short peptides capped at their N-terminus are often highly efficient gelators, yet notoriously difficult to crystallize. This is due to strong unidirectional interactions within fibers, resulting in structure propagation only along one direction. Here, we synthesize the N-capped dipeptide, benzimidazole-diphenylalanine, which forms both hydrogels and single crystals. Even more remarkably, we show using atomic force microscopy the coexistence of these two distinct phases. We then use powder X-ray diffraction to investigate whether the single crystal structure can be extrapolated to the molecular arrangement within the hydrogel. The results suggest parallel β-sheet arrangement as the dominant structural motif, challenging existing models for gelation of short peptides, and providing new directions for the future rational design of short peptide gelators.
AB - Short peptides capped at their N-terminus are often highly efficient gelators, yet notoriously difficult to crystallize. This is due to strong unidirectional interactions within fibers, resulting in structure propagation only along one direction. Here, we synthesize the N-capped dipeptide, benzimidazole-diphenylalanine, which forms both hydrogels and single crystals. Even more remarkably, we show using atomic force microscopy the coexistence of these two distinct phases. We then use powder X-ray diffraction to investigate whether the single crystal structure can be extrapolated to the molecular arrangement within the hydrogel. The results suggest parallel β-sheet arrangement as the dominant structural motif, challenging existing models for gelation of short peptides, and providing new directions for the future rational design of short peptide gelators.
UR - http://www.scopus.com/inward/record.url?scp=84960328063&partnerID=8YFLogxK
U2 - 10.1021/acs.langmuir.5b03963
DO - 10.1021/acs.langmuir.5b03963
M3 - Article
C2 - 26890360
SN - 0743-7463
VL - 32
SP - 2245
EP - 2250
JO - Langmuir
JF - Langmuir
IS - 9
ER -