title: Retinoylserine and retinoylalanine, natural products of the moth Trichoplusia ni.
abstract: Insect cells convert vitamin A into a number of retinoids that are evolutionarily conserved with those of mammalian cells. However, insect cells also produce additional natural retinoids. Namely, two retinoic acid peptides, N-trans-retinoylserine (1) and N-trans-retinoylalanine (2), have been isolated from a cell line of the common cabbage looper, Trichoplusia ni. These are the first examples of naturally occurring retinoic acid linked to amino acids through an amide bond; the amino acid moieties are depicted in the more common l-configuration, although the absolute configuration was not determined due to the minuscule sample amount.
authors.affiliation: Immunology Program, Memorial Sloan-Kettering Cancer Center, New York, New York 10021, USA.
authors.forename: Barbara
authors.initials: B
authors.lastname: Rogge
authors.forename: Yasuhiro
authors.initials: Y
authors.lastname: Itagaki
authors.forename: Nathan
authors.initials: N
authors.lastname: Fishkin
authors.forename: Ester
authors.initials: E
authors.lastname: Levi
authors.forename: Ralph
authors.initials: R
authors.lastname: Rühl
authors.forename: San-San
authors.initials: SS
authors.lastname: Yi
authors.forename: Koji
authors.initials: K
authors.lastname: Nakanishi
authors.forename: Ulrich
authors.initials: U
authors.lastname: Hammerling
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification; D000818:Animals; D002845:Chromatography; D015394:Molecular Structure; D009036:Moths / Q000737:chemistry*; D012694:Serine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism; D014212:Tretinoin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification
chemical_list: C505678:retinoylalanine; C505677:retinoylserine; D012694:Serine; D014212:Tretinoin; D000409:Alanine