N-α-(9-Fluorenylmethoxycarbonyl)-α-methyl-D-α-(7-octenyl)glycine
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N-α-(9-Fluorenylmethoxycarbonyl)-α-methyl-D-α-(7-octenyl)glycine

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(2R)-2-[[(9H-Fluoren-9-ylmethoxy)carbonyl]amino]-2-methyl-9-decenoic Acid, is a stable antimicrobial peptide, that can be isolated from the venom of wild bee Lasioglossum laticeps.

Category
Fmoc-Amino Acids
Catalog number
BAT-005486
CAS number
945212-26-0
Molecular Formula
C26H31NO4
Molecular Weight
421.53
N-α-(9-Fluorenylmethoxycarbonyl)-α-methyl-D-α-(7-octenyl)glycine
IUPAC Name
(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methyldec-9-enoic acid
Synonyms
Fmoc-D-(Me)Gly(Octenyl)-OH; N-α-(9-Fluorenylmethoxycarbonyl)-α-(7-octenyl)-L-alanine; (2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methyldec-9-enoic acid
Appearance
Off-white solid
Purity
≥ 95%
Density
1.140 g/cm3
Boiling Point
588.3±45.0 °C
Storage
Store at -20 °C
InChI
InChI=1S/C26H31NO4/c1-3-4-5-6-7-12-17-26(2,24(28)29)27-25(30)31-18-23-21-15-10-8-13-19(21)20-14-9-11-16-22(20)23/h3,8-11,13-16,23H,1,4-7,12,17-18H2,2H3,(H,27,30)(H,28,29)/t26-/m1/s1
InChI Key
MADFVGMQNXRFAF-AREMUKBSSA-N
Canonical SMILES
CC(CCCCCCC=C)(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
1.(Acyloxy)alkoxy moiety as amino acids protecting group for the synthesis of (R,R)-2,7 diaminosuberic acid via RCM.
Mollica A1, Feliciani F, Stefanucci A, Fadeev EA, Pinnen F. Protein Pept Lett. 2012 Dec;19(12):1245-9.
A new synthetic pathway is described to prepare asymmetrically protected 2,7-diaminosuberic acid. This strategy exploits (acyloxy)alkoxy promoiety as protecting group and RCM reaction using second generation Grubbs catalyst and provides the trans isomer of (2R,7R)-7-(((9H-fluoren-9-yl)methoxy)carbonylamino)-2-(tert-butoxycarbonylamino)-8- methoxy-8-oxooct-4-enoic acid, which was in turn reduced to obtain (2R,7R)-7-(((9H-fluoren-9-yl)methoxy)carbonylamino)- 2-(tert-butoxycarbonylamino)-8-methoxy-8-oxooctanoic acid.
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