(S)-Isoserine

Base Information

• Chemical Name: (S)-Isoserine
• CAS No.: 632-13-3
• Molecular Formula: C₃H₇NO₃
• Molecular Weight: 105.093
• Hs Code.: 2922509090
• European Community (EC) Number: 639-468-1
• DSSTox Substance ID: DTXSID60426449
• Nikkaji Number: J35.706E
• Mol file: 632-13-3.mol

Synonyms:L-Isoserine;632-13-3;(S)-Isoserine;(S)-3-Amino-2-hydroxypropanoic acid;(2S)-3-amino-2-hydroxypropanoic acid;Propanoic acid, 3-amino-2-hydroxy-, (2S)-;(S)-3-Amino-2-hydroxypropionic acid;(R)-Isoserine;s-isoserine;MFCD03428326;(S)-2-Hydroxy-A-alanine;SCHEMBL3347615;DTXSID60426449;BMYNFMYTOJXKLE-REOHCLBHSA-N;BCP22730;3-amino-(2s)-hydroxypropionic acid;AM1113;L-Isoserine, >=98.0% (TLC);AKOS005137983;2-(S)-hydroxy-3-amino-propionic acid;3-amino-2-(S)-hydroxy-propionic acid;CS-W013683;HY-W012967;AS-13397;I0828;EN300-112001;A834279

Chemical Property of (S)-Isoserine

Chemical Property:

• Vapor Pressure: 1.43E-07mmHg at 25°C
• Melting Point: 199-201oC (dec)
• Refractive Index: 1.519
• Boiling Point: 386.6oC at 760 mmHg
• PKA: pK1:2.72(＋1);pK2:9.25(0) (25°C,μ=0.16)
• Flash Point: 187.6oC
• PSA: 83.55000
• Density: 1.415g/cm3
• LogP: -0.90910
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Sensitive.: Moisture Sensitive
• Water Solubility.: Slightly soluble in water.
• XLogP3: -4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 105.042593085
• Heavy Atom Count: 7
• Complexity: 72.6

Purity/Quality:

98% ^*data from raw suppliers

(S)-Isoserine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C(C(=O)O)O)N
• Isomeric SMILES: C([C@@H](C(=O)O)O)N
• Uses: It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuffs.

Technology Process of (S)-Isoserine

There total 3 articles about (S)-Isoserine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

haloirciniamide A → (S)-2,3-diaminopropionic acid (515-94-6,1915-96-4,4033-39-0,6018-54-8) + L-isoserine (565-71-9,632-11-1,632-12-2,632-13-3) + (2R)-aspartic acid (1783-96-6,25608-40-6,27881-03-4,32505-46-7,52526-39-3)

Guidance literature:

haloirciniamide A; With hydrogenchloride; In water; at 110 ℃; for 15h;

With sodium hydrogencarbonate; N-(2,4-dinitro-5-fluorophenyl)-L-alaninamide; In water; acetone; at 40 ℃; for 1h;

DOI:10.3390/MD18080396

Reference yield:

(11S)-cyclocinamide A (194427-76-4) → (S)-2,3-diaminopropionic acid (515-94-6,1915-96-4,4033-39-0,6018-54-8) + L-isoserine (565-71-9,632-11-1,632-12-2,632-13-3) + L-Aspartic acid (56-84-8,25608-40-6,27881-03-4,32505-46-7,52526-39-3) + 5-bromo-DL-tryptophan (6548-09-0,25197-99-3,93299-40-2)

Guidance literature:

With hydrogenchloride; water; In phenol; at 110 ℃; for 4h; Inert atmosphere;

DOI:10.1021/ol300576n

Reference yield:

theonellamide I → L-serin (56-45-1,83245-15-2) + L-isoserine (565-71-9,632-11-1,632-12-2,632-13-3) + (2S,3S)-2-amino-3-hydroxybutanoic acid (28954-12-3,134357-96-3,7013-32-3,82822-12-6) + β-L-arabinopyranose (7296-56-2) + L-asparagine (70-47-3,28088-48-4,7006-34-0) + L-homoglutamic acid (1118-90-7) + L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) + 2-(S)-amino-3-(R)-hydroxysuccinic acid (7298-98-8) + τ-L-histidino-D-alanine (141949-35-1) + H-p-BrPhe-OH (24250-84-8) + (3S,4R)-3-amino-4-hydroxy-6-methyl-8-phenyloctanoic acid

Guidance literature:

With hydrogenchloride; water; at 110 ℃; for 3h;

DOI:10.1021/acs.jnatprod.8b00591

upstream raw materials:

(11S)-cyclocinamide A

Downstream raw materials:

(3S)-α-<(p-benzyloxy)phenyl>-N-(diphenylmethyl)-3-hydroxy-2-oxo-1-azedineacetamide

(2S)-3-{[(benzyloxy)carbonyl]amino}-2-hydroxypropanoic acid

N-(9-Fluorenylmethoxycarbonyl)isoserine

(S)-3-(Dimethylamino)-2-hydroxypropanoic acid

Refernces

• 1、 Fukuhara, Kazuya,Takada, Kentaro,Watanabe, Ryuichi,Suzuki, Toshiyuki,Okada, Shigeru,Matsunaga, Shigeki. "Colony-wise Analysis of a Theonella swinhoei Marine Sponge with a Yellow Interior Permitted the Isolation of Theonellamide i". . p. 2595 - 2599. Retrieved 2018/12/13.