D,L-3-Indolylglycine - CAS 6747-15-5
Catalog number:
6747-15-5
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C10H10N2O2
Molecular Weight:
190.2
COA:
Inquire
Targets:
Others
Description:
D, L-3-Indolylglycine, similar to Tryptophan, is an unnatural amino acid.
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Purity:
≥95%
Appearance:
White to Off White Solid
Synonyms:
Amino-(1H-indol-3-yl)acetic acid; 2-amino-2-(1H-indol-3-yl)acetic acid;
Solubility:
Soluble in DMSO
Storage:
Store at -20 °C
MSDS:
Inquire
Application:
An unnatural amino acid
Quality Standard:
Enterprise Standard
Shelf Life:
As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly
Quantity:
Milligrams-Grams
Melting Point:
203-208 °C
InChIKey:
AIZGBPJAKQNCSD-UHFFFAOYSA-N
InChI:
1S/C10H10N2O2/c11-9(10(13)14)7-5-12-8-4-2-1-3-6(7)8/h1-5,9,12H,11H2,(H,13,14)
Canonical SMILES:
C1=CC=C2C(=C1)C(=CN2)C(C(=O)O)N
1.Crystal structure of an indole-3-acetic acid amido synthetase from grapevine involved in auxin homeostasis.
Peat TS1, Böttcher C, Newman J, Lucent D, Cowieson N, Davies C. Plant Cell. 2012 Nov;24(11):4525-38. doi: 10.1105/tpc.112.102921. Epub 2012 Nov 6.
Auxins are important for plant growth and development, including the control of fruit ripening. Conjugation to amino acids by indole-3-acetic acid (IAA)-amido synthetases is an important part of auxin homeostasis. The structure of the auxin-conjugating Gretchen Hagen3-1 (GH3-1) enzyme from grapevine (Vitis vinifera), in complex with an inhibitor (adenosine-5'-[2-(1H-indol-3-yl)ethyl]phosphate), is presented. Comparison with a previously published benzoate-conjugating enzyme from Arabidopsis thaliana indicates that grapevine GH3-1 has a highly similar domain structure and also undergoes a large conformational change during catalysis. Mutational analyses and structural comparisons with other proteins have identified residues likely to be involved in acyl group, amino acid, and ATP substrate binding. Vv GH3-1 is a monomer in solution and requires magnesium ions solely for the adenlyation reaction. Modeling of IAA and two synthetic auxins, benzothiazole-2-oxyacetic acid (BTOA) and 1-naphthaleneacetic acid (NAA), into the active site indicates that NAA and BTOA are likely to be poor substrates for this enzyme, confirming previous enzyme kinetic studies.
2.Novel (E)-alpha-[(1H-indol-3-yl)methylene]benzeneacetic acids as endothelin receptor ligands.
Pittalà V1, Romeo G, Materia L, Salerno L, Siracusa MA, Modica M, Mereghetti I, Cagnotto A, Russo F. Farmaco. 2005 Sep;60(9):731-8.
Endothelin-1 (ET-1), a peptide of 21 amino acid residues, is the most potent vasoconstrictor substance known and now it is understood to be one of a family of three mammalian vasoactive peptides that also includes ET-2 and ET-3. The endothelins (ETs) affect multiple organ systems and seem to be involved in the pathogenesis of many diseases such as hypertension, pulmonary hypertension, atherosclerosis, apoptosis inhibition and angiogenesis. The ETs exert their effects via activation of two distinct G-protein coupled receptor subtypes termed ET(A) and ET(B). To date a number of ET receptor ligands with good affinity and selectivity is known, nevertheless these compounds belong only to few chemical classes. The aim of this work was the identification of a "hit compound" with novel chemical structure, endowed with reasonable ET affinity and selectivity. Accordingly, a new class of (E)-alpha-[(1H-indol-3-yl)methylene]benzeneacetic acid derivatives (1-23) was synthesized for evaluation of their binding profiles.
3.Evolution of novel tricyclic CRTh2 receptor antagonists from a (E)-2-cyano-3-(1H-indol-3-yl)acrylamide scaffold.
Valdenaire A1, Pothier J, Renneberg D, Riederer MA, Peter O, Leroy X, Gnerre C, Fretz H. Bioorg Med Chem Lett. 2013 Feb 15;23(4):944-8. doi: 10.1016/j.bmcl.2012.12.050. Epub 2012 Dec 25.
(E)-2-(3-(3-((3-Bromophenyl)amino)-2-cyano-3-oxoprop-1-en-1-yl)-1H-indol-1-yl)acetic acid (1) was discovered in a HTS campaign for CRTh2 receptor antagonists. An SAR around this hit could be established and representatives with interesting activity profiles were obtained. Ring closing tactics to convert this hit series into a novel 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole based CRTh2 receptor antagonist series is presented.
4.A novel tool for studying auxin-metabolism: the inhibition of grapevine indole-3-acetic acid-amido synthetases by a reaction intermediate analogue.
Böttcher C1, Dennis EG, Booker GW, Polyak SW, Boss PK, Davies C. PLoS One. 2012;7(5):e37632. doi: 10.1371/journal.pone.0037632. Epub 2012 May 23.
An important process for the regulation of auxin levels in plants is the inactivation of indole-3-acetic acid (IAA) by conjugation to amino acids. The conjugation reaction is catalysed by IAA-amido synthetases belonging to the family of GH3 proteins. Genetic approaches to study the biological significance of these enzymes have been hampered by large gene numbers and a high degree of functional redundancy. To overcome these difficulties a chemical approach based on the reaction mechanism of GH3 proteins was employed to design a small molecule inhibitor of IAA-amido synthetase activity. Adenosine-5'-[2-(1H-indol-3-yl)ethyl]phosphate (AIEP) mimics the adenylated intermediate of the IAA-conjugation reaction and was therefore proposed to compete with the binding of MgATP and IAA in the initial stages of catalysis. Two grapevine IAA-amido synthetases with different catalytic properties were chosen to test the inhibitory effects of AIEP in vitro.
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CAS 6747-15-5 D,L-3-Indolylglycine

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