Ac-Gly-Gly-OH
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Ac-Gly-Gly-OH

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Category
Others
Catalog number
BAT-004916
CAS number
5687-48-9
Molecular Formula
C6H10N2O4
Molecular Weight
174.16
Ac-Gly-Gly-OH
IUPAC Name
2-[(2-acetamidoacetyl)amino]acetic acid
Synonyms
Acetyl-glycylglycine
Appearance
White to off-white powder
Purity
≥ 98% (HPLC)
Density
1.298 g/cm3
Melting Point
178-179°C
Boiling Point
599.6±35.0 °C(Predicted)
Storage
Store at 2-8°C
InChI
InChI=1S/C6H10N2O4/c1-4(9)7-2-5(10)8-3-6(11)12/h2-3H2,1H3,(H,7,9)(H,8,10)(H,11,12)
InChI Key
ZCASHLUDUSAKNN-UHFFFAOYSA-N
Canonical SMILES
CC(=O)NCC(=O)NCC(=O)O
1. Dipeptide binding in water by a de novo designed guanidiniocarbonylpyrrole receptor
Carsten Schmuck, Lars Geiger J Am Chem Soc. 2004 Jul 28;126(29):8898-9. doi: 10.1021/ja048587v.
A new dipeptide receptor 9, which was designed de novo based on theoretical calculations, efficiently binds dipeptides in water with Kass > 104 M-1 by a combination of ion pairing and hydrogen bonds as can be shown by UV-titration and NMR experiments.
2. One-armed artificial receptors for the binding of polar tetrapeptides in water: probing the substrate selectivity of a combinatorial receptor library
Carsten Schmuck, Martin Heil Chemistry. 2006 Feb 1;12(5):1339-48. doi: 10.1002/chem.200501062.
We have recently developed a new class of one-armed artificial receptors 1 for the binding of the polar tetrapeptide N-Ac-D-Glu-L-Lys-D-Ala-D-Ala-OH (EKAA) 2 in water using a combined combinatorial and statistical approach. We have now further probed the substrate selectivity of this receptor library 1 by screening a second tetrapeptide substrate (3) with the inverse sequence N-Ac-D-Ala-D-Ala-L-Lys-D-Glu-OH (AAKE). This "inverse" substrate is also efficiently bound by our receptors, with K(ass) approximately 6000 M(-1) for the best receptors, as determined both by a quantitative on-bead binding assay and by UV and fluorescence titration studies in free solution. Hence, the inverse tetrapeptide 3 is in general bound two to three times less efficiently than the "normal" peptide 2 (K(ass) approximately 17,000 M(-1)), even though the complexation mainly involves long-range electrostatic interactions and both the receptor and substrate are rather flexible. Molecular modeling and ab initio calculations have been used to rationalize the observed substrate selectivity and to analyze the various binding interactions within the complex.
3. Synthesis of a new artificial host for the binding of dipeptides in water
Carsten Schmuck, Laura Hernandez-Folgado Org Biomol Chem. 2007 Aug 7;5(15):2390-4. doi: 10.1039/b707873k. Epub 2007 Jun 22.
An artificial peptide receptor was prepared by a simple procedure. Initial binding studies (UV titrations) in buffered water showed preferential complexation of N-acetyl-dipeptide carboxylates containing alanine in the C-terminal position in comparison with simple amino acids, other dipeptides and two tripeptides.
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