44902-01-4

Basic information

• Product Name: R-2-Aminoheptanoic acid
• Synonyms: R-2-Aminoheptanoic acid;D-Homonorleucine;REF DUPL: R-2-Aminoheptanoic acid;R-2-AMinoheptanoic acid R-2-AMinoheptanoic acid
• CAS NO: 44902-01-4
• Molecular Formula: C₇H₁₅NO₂
• Molecular Weight: 145.1995
• Mol File: 44902-01-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 251.0±23.0 °C(Predicted)
• Appearance: /
• Density: 1.017±0.06 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 2.55±0.24(Predicted)
• CAS DataBase Reference: R-2-Aminoheptanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: R-2-Aminoheptanoic acid(44902-01-4)
• EPA Substance Registry System: R-2-Aminoheptanoic acid(44902-01-4)

Safety Data

• Hazardous Substances Data: 44902-01-4(Hazardous Substances Data)

Usage

General Description

R-2-Aminoheptanoic acid is an organic chemical compound, which features in the category of α-amino acids and derivatives. It is also known as L-2-Aminonanoic acid or L-Norleucine. It is predominantly used in the field of scientific research. It contains a chiral carbon atom at the second position with an amino group (-NH2) and a carboxyl group (-COOH), which are characteristics of alpha amino acid. Its molecular formula is C7H15NO2. R-2-Aminoheptanoic acid is highly soluble in water, and although it's considered part of the amino acid family of chemicals, it is not encoded into proteins in living organisms. As with other chemicals, it should be handled carefully as it can be harmful if it comes into contact with the skin, or if it is inhaled or swallowed.

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Relevant articles and documents

Creation of a broad-range and highly stereoselective D-amino acid dehydrogenase for the one-step synthesis of D-amino acids

Using both rational and random mutagenesis, we have created the first known broad substrate range, nicotinamide cofactor dependent, and highly stereoselective D-amino acid dehydrogenase. This new enzyme is capable of producing D-amino acids via the reductive amination of the corresponding 2-keto acid with ammonia. This biocatalyst was the result of three rounds of mutagenesis and screening performed on the enzyme meso-diaminopimelate D-dehydrogenase. The first round targeted the active site of the wild-type enzyme and produced mutants that were no longer strictly dependent on the native substrate. The second and third rounds produced mutants that had an increased substrate range including straight-and branched-aliphatic amino acids and aromatic amino acids. The very high selectivity toward the D-enantiomer (95 to >99% ee) was shown to be preserved even after the addition of the five mutations found in the three rounds of mutagenesis and screening. This new enzyme could complement and improve upon current methods for D-amino acid synthesis.

Conversion of Serine β-Lactones to Chiral α-Amino Acids by Copper-Containing Organolithium and Organomagnesium Reagents

A method for the synthesis of optically pure α-amino acids has been developed.Mono- and di-N-protected α-amino-β-lactones 3a (L, R1=H, R2=COOCH2Ph (Z)), 3b (D, R1=H, R2=Z), 3c (L, R1=CH2Ph, R2=Z), and 3d (D, R1=CH2Ph, R2=Z) are readily produced by cyclization of the corresponding serine derivatives 2 under modified Mitsunobu conditions without loss of optical purity.Stereochemical integrity was demonstrated by conversion of 3 to 2-methoxy-2-(trifluoromethyl)phenylacetate esters 6 and analysis by HPLC, (19)F NMR, and (1)H NMR.Reaction of 3 with organolithium-derived cuprate reagents (R2CuLi or R2Cu(CN)Li2) at low temperature produces N-protected α-amino acids by attack at the β-methylene group.Yields of di-N-protected amino acids are generally higher (ca. 50-75percent), but some decrease in enantiomeric excess (ee) can occur (0-27percent).In contrast, the mono-N-protected β-lactones 3a and 3b give slightly lower yields (ca. 44-62percent) but negligible decrease in ee (0-1.7percent) with the exception of Ph2Cu(CN)Li2 (67percent loss of ee).However, the use of Cu(I)-catalyzed Grignard (RMgCl) additions gives better yields (44-83percent), complete retention of optical purity ( 99.4percent), and fewer side products.Reductive removal of the protecting groups in a single step (H2/Pd-C or Na/NH3) affords the free α-amino acids in 91-99percent yield.Their stereochemical purity was determined by conversion to the corresponding N-(-)-camphanoyl methyl esters and analysis by gas chromatography and (1)H NMR spectroscopy.