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Transitions of saturated monoacid triglycerides: Modeling conformational change at glycerol during α→β′→β transformation
Author(s) -
Hagemann J. W.,
Rothfus J. A.
Publication year - 1993
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02545297
Subject(s) - bent molecular geometry , chain (unit) , chemistry , side chain , glycerol , differential scanning calorimetry , double bond , rotation (mathematics) , transformation (genetics) , energy transformation , chemical physics , crystallography , thermodynamics , organic chemistry , geometry , physics , polymer , mathematics , biochemistry , astronomy , gene
The glycerol region geometry of modeled saturated monoacid triglycerides was altered by bond rotations and minor angle distortions to convert theoretical α‐forms into bent β′‐ and β‐forms. Direct α to β conversion involves lateral disruption of fatty chain packing to generate side‐chain character typical of the β‐form. Such disruption, which could contribute to fat bloom, allows additional molecular movement and shifts in molecular mechanics energy (MME) that may approximate thermal changes observed by differential scanning calorimetry during α to β transformations. Energy calculations at 100 points throughout each transformation identified plausible conversion routes. A two‐stage conversion, α to either of two stereospecific β′‐forms bent at glycerol followed by subsequent conversion to β, showed less chain movement and more favorable MME than direct α to β conversion. The preferred path, based on energy profiles of each conversion, involves a β′‐D form and rotation of carbonyl to α‐carbon bonds in chain #2 and a side chain (chain #3).