632-11-1

Basic information

• Product Name: (R)-Isoserine
• Synonyms: (R)-ISOSERINE;(S)-IsoserineL-Isoserine;(2R)-3-AMINO-2-HYDROXY-PROPANOIC ACID;(+)-3-Amino-D-lactic acid;(R)-3-Amino-2-hydroxypropanoic acid;(R)-3-Amino-2-hydroxypropionic acid;[R,(+)]-3-Amino-2-hydroxypropionic acid
• CAS NO: 632-11-1
• Molecular Formula: C₃H₇NO₃
• Molecular Weight: 105.09
• Product Categories: Amino acids, non natural;Chiral Compounds
• Mol File: 632-11-1.mol
• Article Data: 3

Chemical Properties

• Melting Point: 197-198 °C
• Boiling Point: 386.6 °C at 760 mmHg
• Flash Point: 187.6 °C
• Appearance: /
• Density: 1.415 g/cm³
• Vapor Pressure: 1.43E-07mmHg at 25°C
• Refractive Index: 1.519
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 2.71±0.16(Predicted)
• CAS DataBase Reference: (R)-Isoserine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-Isoserine(632-11-1)
• EPA Substance Registry System: (R)-Isoserine(632-11-1)

Safety Data

• Hazardous Substances Data: 632-11-1(Hazardous Substances Data)

Usage

General Description

(R)-Isoserine, also known as D-Isoserine, is a chemical compound that belongs to the class of organic compounds known as L-alpha-amino acids. It is an enantiomer of a isoserine, which means it is one of two stereoisomers that are mirror images of each other. It does not possess a chiral center, rendering it incapable of exhibiting isomerism. (R)-Isoserine is used in pharmaceutical settings often, and used as the basic building block for a number of biologically active compounds, including antibiotic synthesis. It may also have potential therapeutic uses, due to its interactions with various biological systems.

InChI:InChI=1/C3H7NO3/c4-1-2(5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m1/s1

Upstream product

• 194427-76-4 (11S)-cyclocinamide A 

Downstream Products

• 73739-18-1 (R)-3-benzoyl-oxazolidine-5-carboxylic acid 
• 88147-46-0 (3R)-α-<(p-benzyloxy)phenyl>-N-(diphenylmethyl)-3-hydroxy-2-oxo-1-azedineacetamide 
• 88147-46-0 (3S)-α-<(p-benzyloxy)phenyl>-N-(diphenylmethyl)-3-hydroxy-2-oxo-1-azedineacetamide 
• 78771-78-5 N-(Diphenelmethyl)-3-hydroxy-2-oxo-α-phenyl-1-azetidineacetamide 
• 52558-23-3 (R)-3-(tert-butoxycarbonylamino)-2-hydroxypropanoic acid 
• 52558-24-4 (s)-3-tert-butoxycarbonylamino-2-hydroxypropionic acid 
• 42491-79-2 (2S)-3-{[(benzyloxy)carbonyl]amino}-2-hydroxypropanoic acid 
• 161125-36-6 N-(9-Fluorenylmethoxycarbonyl)isoserine 
• 140372-10-7 (S)-3-(Dimethylamino)-2-hydroxypropanoic acid 
• 125496-24-4 N,O-diformyl-(S)-isoserine 
• 1455086-89-1 2-(S)-hydroxy-3-[(4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]propionic acid 
• 1455089-11-8 2-(S)-hydroxy-3-{[4-hydroxy-7-(4-methoxyphenoxy)isoquinoline-3-carbonyl]amino}propionic acid 
• 1455088-62-6 3-[(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carbonyl)amino]-2-(S)-hydroxypropionic acid 
• 133319-36-5 N-phthaloyl-L-isoserine 

Relevant articles and documents

Unique polyhalogenated peptides from the marine sponge Ircinia sp.

Two new bromopyrrole peptides, haloirciniamide A (1) and seribunamide A (2), have been isolated from an Indonesian marine sponge of the genus Ircinia collected in the Thousand Islands (Indonesia). The planar structure of both compounds was assigned on the basis of extensive 1D and 2D NMR spectroscopy and mass spectrometry. The absolute configuration of the amino acid residues in 1 and 2 was determined by the application of Marfey's method. Compound 1 is the first dibromopyrrole cyclopeptide having a chlorohistidine ring, while compound 2 is a rare peptide possessing a tribromopyrrole ring. Both compounds failed to show significant cytotoxicity against four human tumor cell lines, and neither compound was able to inhibit the enzyme topoisomerase I or impair the interaction between programmed cell death protein PD1 and its ligand, PDL1.

Total synthesis of nominal (11S)- and (11R)-cyclocinamide A

The cyclocinamides possess a unique β2αβ 2α 14-membered tetrapeptide core. The initially reported biological data and intriguing structure, which was without full stereochemical identification, necessitated synthesis of both nominal (all-S) cyclocinamide A and the 11R isomer. The completed synthesis is highlighted by the use of a (cyclo)asparagine-containing dipeptide as a turn inducing fragment. Due to inconsistencies in analytical data between natural and synthetic samples, a re-evaluation of the natural product stereochemistry appears necessary.