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Chemical structure of Fmoc-Asp(OtBu)-(Hmb)Gly-OH

GA21539

Fmoc-Asp(OtBu)-(Hmb)Gly-OH

Also known as 2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-[(2-methylpropan-2-yl)oxy]-4-oxobutanoyl]-[(2-hydroxy-4-methoxyphenyl)methyl]amino]acetic acid

Aspartimide formation of the highly base-labile Asp-Gly motif during Fmoc-SPPS may be completely suppressed by coupling this Hmb-protected dipeptide derivative· Additionally, Hmb prevents aggregation of the growing peptide chain as efficiently as the incorporation of a pseudoproline moiety· O-Acylation renders the Hmb moiety acid-stable facilitating the purification of peptides prone to form aggregates· The acyl group can be removed with hydrazine hydrate in DMF (cf· Quibell)

ChemicalCAS502640-94-0MW604.67FormulaC33H36N2O9
CAS number
502640-94-0
Molecular weight
604.67
Formula
C33H36N2O9
Solubility
Soluble in DMSO
InChIKey
XDJHXXOYIQLAEM-MHZLTWQESA-N
Catalogue number
GA21539
Brand
GLPBIO
Computed properties PubChem CID 2756239 · XLogP 4.1 · TPSA 152 Ų · H-bond donors 3
XLogP
4.1
TPSA
152 Ų
H-bond donors
3
H-bond acceptors
9
Rotatable bonds
14
Heavy atoms
44

SMILES CC(C)(C)OC(=O)C[C@@H](C(=O)N(CC1=C(C=C(C=C1)OC)O)CC(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

Computed descriptors from PubChem (CID 2756239), public domain. Identity cross-checked against the supplier's molecular formula and weight — verify before use.

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