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

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

(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

Amino Acids for Stapled Peptide

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

Specification
Reference Reading

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.