Fmoc-D-Dap(Ac)-OH
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Fmoc-D-Dap(Ac)-OH

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Category
Fmoc-Amino Acids
Catalog number
BAT-001860
CAS number
1313054-72-6
Molecular Formula
C20H20N2O5
Molecular Weight
368.4
IUPAC Name
(2R)-3-acetamido-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
Synonyms
3-(Acetylamino)-N-Fmoc-D-alanine; (2R)-3-acetamido-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)propanoic acid
Purity
≥ 95%
InChI
InChI=1S/C20H20N2O5/c1-12(23)21-10-18(19(24)25)22-20(26)27-11-17-15-8-4-2-6-13(15)14-7-3-5-9-16(14)17/h2-9,17-18H,10-11H2,1H3,(H,21,23)(H,22,26)(H,24,25)/t18-/m1/s1
InChI Key
NJHKPVSGTKWJEN-GOSISDBHSA-N
Canonical SMILES
CC(=O)NCC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
1. Inter- and intraspecific activities of compounds derived from sex pheromone glands of currant borer, Synanthedon tipuliformis (Clerck) (Lepidoptera: Sesiidae)
Raimondas Mozŭraitis, Vidmantas Karalius, Vincas Bŭda, Anna-Karin Borg-Karlson Z Naturforsch C J Biosci. 2006 Mar-Apr;61(3-4):278-84. doi: 10.1515/znc-2006-3-421.
Gas chromatography and mass spectrometry analyses of crude sex pheromone gland extracts revealed that virgin Synanthedon tipuliformis (Clerck), currant borer (Lepidoptera: Sesiidae) females, produced 6 compounds, structurally related to sex pheromone components of clearwing moths. By comparison of retention times and mass spectra of natural products with corresponding properties of synthetic standards, these compounds were identified as: (2E,13Z)-octadeca-2,13-dien-1-yl acetate (E2,Z13-18:OAc), (3E,13Z)-octadeca-3,13-dien-1-yl acetate (E3,Z13-18:OAc), (13Z)-octadec-13-en-1-yl acetate (Z13-18:OAc), (2E,13Z)-octadeca-2,13-dien-1-ol (E2,Z13-18:OH), (13Z)-octadec-13-en-1-ol (Z13-18:OH) and octadecan-1-ol (18:OH) in the ratio 100:0.7:2.7:3.2:traces:traces. The first 3 compounds were previously known to occur in the sex pheromone gland extracts of currant borers, while the last 3 chemicals are now reported for the first time. Trapping tests carried out in the black currant field revealed that E2,Z13-18:OAc, when tested separately, attracted S. tipuliformis males, while addition of E3,Z13-18:OAc to the main component increased the effectiveness of E2,Z13-18:OAc over seven times. The attractiveness of 6 component lures did not differ significantly from the one of the binary mixture, confirming that E2,Z13-18:OAc and E3,Z13-18:OAc in the ratio100:0.7 are essential sex pheromone components of S. tipuliformis. Trapping tests carried out at the dwelling place of Synanthedon scoliaeformis (Borkhausen) (Lepidoptera: Sesiidae) revealed that, in addition to intraspecific synergistic effect, E3,Z13-18:OAc increased the specificity of the pheromone signal of S. tipuliformis, acting by intraspecific mode as an attraction antagonist against S. scoliaeformis males. By this way, it ensured the specificity of the sex attraction signal of the currant borer. Consequently, both compounds E2,Z13-18:OAc and E3,Z13-18:OAc have to be present in pheromone formulations used for monitoring and/or control of S. tipuliformis to avoid effecting non-target species. Other compounds identified from the sex pheromone gland of S. tipuliformis did not show any significant interspecific activity for males of S. scoliaeformis, however, they provide a basis to achieve specificity of a pheromone signal of S. tipuliformis and could act as attraction antagonists against other clearwing moth species which, like S. tipuliformis, employ E2,Z13-18:OAc as their sex pheromone component.
2. Sex attractants for six moth species of the families Brachodidae, Choreutidae and Tineidae from Kazakhstan and Lithuania
Vidmantas Karalius, Raimondas Mozŭraitis, Vincas Bŭda, Ilme Libikas, Anna-Karin Borg-Karlson Z Naturforsch C J Biosci. 2005 Jul-Aug;60(7-8):625-31. doi: 10.1515/znc-2005-7-819.
Sex attractants were established for one Brachodidae, three Choreutidae and two Tineidae moth species during field screening tests with (2E,13Z)-octadecadien-1-al, (2E,13Z)-, (3E,13Z)-, (3Z,13Z)-octadecadien-1-ols and their acetates (2E,13Z-18:Ald, 2E,13Z-, 3E,13Z-, 3Z,13Z-18:OH/OAc) as well as of binary mixtures of these compounds in West-Kazakhstan and Lithuania. Males of Brachodes appendiculata were attracted by 3E,13Z-18:OAc, Prochoreutis ultimana and P. myllerana by 2E,13Z-18:OH, Monopis palidella by 2E,13Z-18:Ald and Triaxomera fulvimitrella by binary mixtures of 3Z,13Z-18:OAc with either 3E,13Z-18:OH in the ratio of 5:5 or 3Z,13Z-18:OH in the ratio of 9:1 (v/v). The 3-component mixture composed of 2E,13Z-18:OH, 3Z,13Z-18:OH and 2E,13Z-18:Ald in the ratio 1:1:1 was developed to attract Prochoreutis sehestediana males. Attraction antagonists for B. appendiculata, P. ultimana and M. palidella were shown.
3. Sex attractants for six clearwing and tineid species (Lepidoptera, Sesiidae and Tineidae) from Kazakhstan and Lithuania
V Karalius, R Mozuraitis, J Miatleuski, V Buda, P Ivinskis Z Naturforsch C J Biosci. 2001 Nov-Dec;56(11-12):1120-5. doi: 10.1515/znc-2001-11-1233.
Sex attractants for 3 Sesiidae and 3 Tineidae moth species in West-Kazakhstan and Lithuania were discovered by field screening tests of (3Z,13Z)-, (3E,13Z)- and (2E,13Z)-octadecadien-1-ols and their acetates as well as of some binary mixtures of these compounds. Total amount of chemicals was 0.3 mg/dispenser. Males of Synanthedon serica were attracted by a 5:5 mixture of 3E,13Z-18:OAc and 2E,13Z-18:OAc, Chamaesphecia bibioniformis by a 9:1 mixture of 3Z,13Z-18:OAc and 3E,13Z-18:OAc, Paranthrene tabaniformis by a 1:9 mixture of 3Z,13Z-18:OH and 3E,13Z-18:OH, Tinea nonimella by a 1:9 mixture of 3E,13Z-18:OH and 2E,13Z-18:OH, Monopis monachella by a 1:9 mixture of 3Z,13Z-18:OH and 2E,13Z-18:OH, and Nemaxera betulinella by a 9:1 mixture of 2E,13Z-18:OAc and the corresponding alcohol. The periods of attraction to the traps were registered for males of S. serica and Ch. bibioniformis and were found to occur at 15-18 and 15-17 o'clock, local time, respectively.
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