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

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

Uses

Used in Pharmaceutical Industry:
(R)-Isoserine is used as a basic building block for the synthesis of various biologically active compounds, including antibiotics. Its role in the pharmaceutical industry is significant as it contributes to the development of new drugs and therapeutic agents.
Used in Therapeutic Applications:
(R)-Isoserine is used as a potential therapeutic agent for various health conditions. Its interactions with different biological systems make it a promising candidate for the treatment of certain diseases and disorders, although further research is needed to fully understand its potential and efficacy in these applications.

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 
• 78771-78-5 N-(Diphenelmethyl)-3-hydroxy-2-oxo-α-phenyl-1-azetidineacetamide 
• 52558-23-3 (R)-3-(tert-butoxycarbonylamino)-2-hydroxypropanoic acid 
• 88147-46-0 (3S)-α-<(p-benzyloxy)phenyl>-N-(diphenylmethyl)-3-hydroxy-2-oxo-1-azedineacetamide 
• 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.

Colony-wise Analysis of a Theonella swinhoei Marine Sponge with a Yellow Interior Permitted the Isolation of Theonellamide i

There are several examples of marine organisms whose metabolic profiles differ among conspecifics inhabiting the same region. We have analyzed the metabolic profile of each colony of a Theonella swinhoei marine sponge with a yellow interior and noticed the patchy distribution of one metabolite. This compound was isolated and its structure was studied by a combination of spectrometric analyses and chemical degradation, showing it to be a congener in the theonellamide class of bicyclic peptides. Theonellamides had previously been isolated by us only from T. swinhoei with a white interior and not from those with a yellow interior.

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.