L-Serinamide

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Category Others
Catalog number BBF-04753
CAS 6791-49-7
Molecular Weight 104.1
Molecular Formula C3H8N2O2

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Specification

Synonyms Serinamide
IUPAC Name (2S)-2-amino-3-hydroxypropanamide
Canonical SMILES C(C(C(=O)N)N)O
InChI InChI=1S/C3H8N2O2/c4-2(1-6)3(5)7/h2,6H,1,4H2,(H2,5,7)/t2-/m0/s1
InChI Key MGOGKPMIZGEGOZ-REOHCLBHSA-N

Properties

Boiling Point 444.7°C at 760 mmHg
Density 1.294 g/cm3

Reference Reading

1. Fourier transform microwave spectroscopy of Ac-Ser-NH2: the role of side chain interactions in peptide folding
Carlos Cabezas, Martinus A T Robben, Anouk M Rijs, Isabel Peña, J L Alonso Phys Chem Chem Phys. 2015 Aug 21;17(31):20274-80. doi: 10.1039/c5cp02654g.
Serine capped dipeptide N-acetyl-l-serinamide (Ac-Ser-NH2) has been investigated using Fourier transform microwave spectroscopic techniques combined with laser ablation sources. Spectral signatures originating from one dominant species have been detected in the supersonic expansion. Rotational and nuclear quadrupole coupling constants of the two (14)N nuclei have been used in the characterization of a C/γ-turn structure, which is stabilized by a CO∙∙∙HN intramolecular hydrogen bond closing a seven-membered ring. Two extra hydrogen bonds involving the polar side chain (-CH2OH) further stabilize the structure. The non-observation of C5 species, attributed to the presence of the polar side chain, is in contrast with the previous gas phase observation of the related dipeptides containing glycine or alanine residues. The A-E splitting pattern arising from the internal rotation of the methyl group has been analyzed and the internal rotation barrier has been determined.

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