An L-alpha-amino acid zwitterion obtained by transfer of a proton from the carboxy group to the amino group of L-beta-ethynylserine. The major species at pH 7.3.

Identification

IUPAC Names

2-azaniumyl-2,4,5-trideoxy-D-threo-pent-4-ynonate

Molecular Formula
C5H7NO3
Mass
129.115
Monoisotopic Mass
129.04259
Charge
0
InChI
InChI=1S/C5H7NO3/c1-2-3(7)4(6)5(8)9/h1,3-4,7H,6H2,(H,8,9)/t3-,4+/m1/s1
InChIKey
RBWXRFBKVDBXEG-DMTCNVIQSA-N
SMILES
[C@@H]([C@@H](C([O-])=O)[NH3+])(O)C#C
Synonyms

(2S,3R)-2-azaniumyl-3-hydroxypent-4-ynoate

L-beta-ethynylserine zwitterion

Species

Europe PubMed Central results


Effective use of computerized insulin dose adjustment algorithms on continuous glucose monitoring results by a clinical pharmacist - Proof-of-concept.

Author: Davidson MB, Davidson SJ.

Abstract: Highlights A clinical pharmacist using recommendations of Food and Drug Administration-cleared computerized insulin dose adjustment algorithms based on analyses of glucose readings from continuous glucose monitoring (Abbot Free Style Pro) in 13 poorly controlled insulin-requiring diabetic patients increased time in target range of 3.9 to 10.0 mmol/L from 29% to 51% and decreased time in range of >13.9 mmol/L from 43% to 23% (both P = 0.01) after 3 months. Glycated hemoglobin (HbA1c) levels (±SD) fell from 102 (±15) to 67 (±10) mmol/mol (P < 10-6 ).

Discovery of a pathway for terminal-alkyne amino acid biosynthesis.

Author: Marchand JA, Neugebauer ME, Ing MC, Lin CI, Pelton JG, Chang MCY.

Abstract: Living systems can generate an enormous range of cellular functions, from mechanical infrastructure and signalling networks to enzymatic catalysis and information storage, using a notably limited set of chemical functional groups. This observation is especially notable when compared to the breadth of functional groups used as the basis for similar functions in synthetically derived small molecules and materials. The relatively small cross-section between biological and synthetic reactivity space forms the foundation for the development of bioorthogonal chemistry, in which the absence of a pair of reactive functional groups within the cell allows for a selective in situ reaction<sup>1-4</sup>. However, biologically 'rare' functional groups, such as the fluoro<sup>5</sup>, chloro<sup>6,7</sup>, bromo<sup>7,8</sup>, phosphonate<sup>9</sup>, enediyne<sup>10,11</sup>, cyano<sup>12</sup>, diazo<sup>13</sup>, alkene<sup>14</sup> and alkyne<sup>15-17</sup> groups, continue to be discovered in natural products made by plants, fungi and microorganisms, which offers a potential route to genetically encode the endogenous biosynthesis of bioorthogonal reagents within living organisms. In particular, the terminal alkyne has found broad utility via the Cu(I)-catalysed azide-alkyne cycloaddition 'click' reaction<sup>18</sup>. Here we report the discovery and characterization of a unique pathway to produce a terminal alkyne-containing amino acid in the bacterium Streptomyces cattleya. We found that L-lysine undergoes an unexpected reaction sequence that includes halogenation, oxidative C-C bond cleavage and triple bond formation through a putative allene intermediate. This pathway offers the potential for de novo cellular production of halo-, alkene- and alkyne-labelled proteins and natural products from glucose for a variety of downstream applications.