trans-4-Propynyl-L-proline hydrochloride
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trans-4-Propynyl-L-proline hydrochloride

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Category
Alkynyl Amino Acids
Catalog number
BAT-007008
CAS number
1049755-32-9
Molecular Formula
C8H11NO2HCl
Molecular Weight
189.64
trans-4-Propynyl-L-proline hydrochloride
IUPAC Name
(2S,4R)-4-prop-2-ynylpyrrolidine-2-carboxylic acid;hydrochloride
Synonyms
H-Pro(4-Propynyl)-OH HCl; (R)-γ-Propynyl-L-proline HCl; (2S,4R)-4-Propynylpyrrolidine-2-carboxylic acid hydrochloride
Related CAS
1049984-28-2 (free base)
Appearance
White to off-white powder
Purity
≥ 98% (TLC)
Melting Point
140-146 °C
Storage
Store at -20 °C
InChI
InChI=1S/C8H11NO2.ClH/c1-2-3-6-4-7(8(10)11)9-5-6;/h1,6-7,9H,3-5H2,(H,10,11);1H/t6-,7+;/m1./s1
InChI Key
WSLSABJECSWKCW-HHQFNNIRSA-N
Canonical SMILES
C#CCC1CC(NC1)C(=O)O.Cl
1.Discovery of (2S,4R)-1-(2-aminoacetyl)-4-benzamidopyrrolidine-2-carboxylic acid hydrochloride (GAP-134)13, an orally active small molecule gap-junction modifier for the treatment of atrial fibrillation.
Butera JA1, Larsen BD, Hennan JK, Kerns E, Di L, Alimardanov A, Swillo RE, Morgan GA, Liu K, Wang Q, Rossman EI, Unwalla R, McDonald L, Huselton C, Petersen JS. J Med Chem. 2009 Feb 26;52(4):908-11. doi: 10.1021/jm801558d.
Rotigaptide (3) is an antiarrhythmic peptide that improves cardiac conduction by modifying gap-junction communication. Small molecule gap-junction modifiers with improved physical properties were identified from a Zealand Pharma peptide library using pharmaceutical profiling, established SAR around 3, and a putative pharmacophore model for rotigaptide. Activity of the compounds was confirmed in a mouse cardiac conduction block model of arrhythmia. Dipeptide 9f (GAP-134) was identified as a potent, orally active gap-junction modifier for clinical development.
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