Retinoylserine and retinoylalanine, natural products of the moth Trichoplusia ni.
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.
Rogge
Barbara
B
Immunology Program, Memorial Sloan-Kettering Cancer Center, New York, New York 10021, USA.
Itagaki
Yasuhiro
Y
Fishkin
Nathan
N
Levi
Ester
E
Rühl
Ralph
R
Yi
San-San
SS
Nakanishi
Koji
K
Hammerling
Ulrich
U
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
C505678:retinoylalanine; C505677:retinoylserine; D012694:Serine; D014212:Tretinoin; D000409:Alanine