title: Chemical Synthesis and Self-Assembly of a Ladderane Phospholipid.
abstract: Ladderane lipids produced by anammox bacteria constitute some of the most structurally fascinating yet poorly studied molecules among biological membrane lipids. Slow growth of the producing organism and the inherent difficulty of purifying complex lipid mixtures have prohibited isolation of useful amounts of natural ladderane lipids. We have devised a highly selective total synthesis of ladderane lipid tails and a full phosphatidylcholine to enable biophysical studies on chemically homogeneous samples of these molecules. Additionally, we report the first proof of absolute configuration of a natural ladderane.
authors.affiliation: Department of Chemistry, Stanford University , Stanford, California 94305, United States.
authors.forename: Jaron A M
authors.initials: JA
authors.lastname: Mercer
authors.affiliation: Department of Chemistry, Stanford University , Stanford, California 94305, United States.
authors.forename: Carolyn M
authors.initials: CM
authors.lastname: Cohen
authors.affiliation: Department of Chemistry, Stanford University , Stanford, California 94305, United States.
authors.forename: Steven R
authors.initials: SR
authors.lastname: Shuken
authors.affiliation: Department of Chemistry, Stanford University , Stanford, California 94305, United States.
authors.forename: Anna M
authors.initials: AM
authors.lastname: Wagner
authors.affiliation: Department of Chemistry, Stanford University , Stanford, California 94305, United States.
authors.forename: Myles W
authors.initials: MW
authors.lastname: Smith
authors.affiliation: Department of Chemistry, Stanford University , Stanford, California 94305, United States.
authors.forename: Frank R
authors.initials: FR
authors.lastname: Moss
authors.affiliation: Department of Chemistry, Stanford University , Stanford, California 94305, United States.
authors.forename: Matthew D
authors.initials: MD
authors.lastname: Smith
authors.affiliation: Department of Built Environment, School of Engineering, Aalto University, Aalto , FI-00076 Espoo, Finland.
authors.forename: Riku
authors.initials: R
authors.lastname: Vahala
authors.affiliation: Department of Built Environment, School of Engineering, Aalto University, Aalto , FI-00076 Espoo, Finland.
authors.forename: Alejandro
authors.initials: A
authors.lastname: Gonzalez-Martinez
authors.affiliation: Department of Chemistry, Stanford University , Stanford, California 94305, United States.
authors.forename: Steven G
authors.initials: SG
authors.lastname: Boxer
authors.affiliation: Department of Chemistry, Stanford University , Stanford, California 94305, United States.
authors.forename: Noah Z
authors.initials: NZ
authors.lastname: Burns
mesh_terms: D008968:Molecular Conformation; D010743:Phospholipids / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D010743:Phospholipids