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286338

DL-Isoserine

Name: <SC>DL</SC>-Isoserine
Brand: ALDRICH

98%

Synonym(s):

(±)-3-Amino-2-hydroxypropionic acid

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About This Item

Linear Formula:

H₂NCH₂CH(OH)CO₂H

CAS Number:

565-71-9

Molecular Weight:

105.09

UNSPSC Code:

12352209

NACRES:

NA.22

PubChem Substance ID:

24857239

MDL number:

MFCD00008138

Beilstein/REAXYS Number:

1721413

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Properties

Quality Level

100

assay

98%

form

powder

reaction suitability

reaction type: solution phase peptide synthesis

mp

235 °C (dec.) (lit.)

application(s)

peptide synthesis

SMILES string

NCC(O)C(O)=O

InChI

1S/C3H7NO3/c4-1-2(5)3(6)7/h2,5H,1,4H2,(H,6,7)

InChI key

BMYNFMYTOJXKLE-UHFFFAOYSA-N

Description

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Organocatalytic syn-aldol reactions of dioxanones with (S)-isoserinal hydrate: synthesis of L-deoxymannojirimycin and L-deoxyidonojirimycin.

Nagarjuna Palyam et al.

The Journal of organic chemistry, 74(11), 4390-4392 (2009-05-02)

We report a new protocol for synthesis of L-1-deoxymannojirimycin, L-1-deoxyidonojirimycin, and the N-isopropyl derivative of the latter compound from the readily available precursors (S)-isoserinal hydrate and 2-tert-butyl-2-methyl-1,3-dioxan-5-one. The key steps include diastereoselective proline-catalyzed syn aldol transformation and a reductive amination/cyclization.

Substituting isoserine for serine in the thrombin receptor activation peptide SFLLRN confers resistance to aminopeptidase M-induced cleavage and inactivation.

B S Coller et al.

The Journal of biological chemistry, 268(28), 20741-20743 (1993-10-05)

Peptides containing sequences derived from the new NH2 terminus of the seven-transmembrane domain thrombin receptor after thrombin cleavage can activate platelets directly. We recently demonstrated that such peptides are readily cleaved and inactivated by plasma, serum, and endothelial cell-associated aminopeptidase

Asymmetric synthesis of oxazolidine nucleosides and related chemistry.

J Du et al.

Nucleosides & nucleotides, 17(1-3), 1-13 (1998-08-26)

Asymmetric synthesis of N-substituted oxazolidinyl nucleosides has been accomplished from L-isoserine, trans- and cis-Oxazolidine intermediates (4 and 5) were stereoselectively constructed from N-protected L-isoserine with a menthoxycarbonyl group by the condensation with benzoyloxy acetaldehyde dimethyl acetal in a ratio of

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Global Trade Item Number

SKU	GTIN
286338-1G	04061826101285