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Nα-Boc-Nγ-Fmoc-D-2,4-diaminobutyric acid

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Category

BOC-Amino Acids

Catalog number

BAT-005655

CAS number

131570-57-5

Molecular Formula

C24H28N2O6

Molecular Weight

440.50

Nα-Boc-Nγ-Fmoc-D-2,4-diaminobutyric acid

Specification
Reference Reading

IUPAC Name

(2R)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid

Synonyms

Boc-D-Dab(Fmoc)-OH

Appearance

White powder

Purity

≥ 99% (HPLC)

Density

1.243g/cm3

Melting Point

123-140 °C

Boiling Point

670.9ºC at 760 mmHg

Storage

Store at 2-8°C

InChI

InChI=1S/C24H28N2O6/c1-24(2,3)32-23(30)26-20(21(27)28)12-13-25-22(29)31-14-19-17-10-6-4-8-15(17)16-9-5-7-11-18(16)19/h4-11,19-20H,12-14H2,1-3H3,(H,25,29)(H,26,30)(H,27,28)/t20-/m1/s1

InChI Key

MJZDTTZGQUEOBL-HXUWFJFHSA-N

Canonical SMILES

CC(C)(C)OC(=O)NC(CCNC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13)C(=O)O

1.Facile synthesis of Nalpha-protected-L-alpha,gamma-diaminobutyric acids mediated by polymer-supported hypervalent iodine reagent in water.

Yamada K1, Urakawa H, Oku H, Katakai R. J Pept Res. 2004 Aug;64(2):43-50.

Hofmann rearrangement of Nalpha-Boc-L-Gln-OH mediated by a polymer-supported hypervalent iodine reagent poly[(4-diacetoxyiodo)styrene] (PSDIB) in water afforded Nalpha-Boc-L-alpha,gamma-diaminobutyric acid (Boc-Dab-OH, 1) in 87% yield. Nalpha-Z-derivative (Z-Dab-OH, 2) was prepared with PSDIB in 83% yield. Since the reaction of Nalpha-Fmoc-Gln-OH by this procedure did not proceed because of the insolubility of Fmoc-Gln-OH in aqueous media, we synthesized Fmoc-Dab(Boc)-OH (5) from 2 in 54% yield. Polymyxin B heptapeptide (PMBH) which contains four Dab residues was successfully synthesized in a solution-phase synthesis.