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Key Documents

D5018

Sigma-Aldrich

3,4-Dehydro-L-proline methyl ester hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C6H9NO2 · HCl
CAS Number:
Molecular Weight:
163.60
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.26

form

solid

storage temp.

−20°C

SMILES string

Cl.COC(=O)C1NCC=C1

InChI

1S/C6H9NO2.ClH/c1-9-6(8)5-3-2-4-7-5;/h2-3,5,7H,4H2,1H3;1H

InChI key

LDWTUXKKNIHFQG-UHFFFAOYSA-N

Biochem/physiol Actions

3,4-Dehydro-L-proline methyl ester is C-terminal blocked 3,4-Dehydro-L-proline (3,4-DHP). 3,4-Dehydro-L-proline is used as a substrate and inhibitor of various enzymes. 3,4-Dehydro-L-proline may be used to inhibit extensin biosynthesis. 3,4-Dehydro-L-proline is a alternate substrate of the amino acid oxidase, NikD. 3,4-Dehydro-L-proline inhibits collagen secretion by chondorcytes.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


Certificates of Analysis (COA)

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Developmental localization and the role of hydroxyproline rich glycoproteins during somatic embryogenesis of banana (Musa spp. AAA).
Xu C, Takac T, Burbach C, et al.
BMC plant biology, 24, 38-38 (2011)
Hyon Jong Kim et al.
The Journal of biological chemistry, 283(16), 10310-10317 (2008-02-19)
Physiological mineralization in growth plate cartilage is highly regulated and restricted to terminally differentiated chondrocytes. Because mineralization occurs in the extracellular matrix, we asked whether major extracellular matrix components (collagens) of growth plate cartilage are directly involved in regulating the
Annick Méjean et al.
Biochemistry, 49(1), 103-113 (2009-12-04)
Anatoxin-a and homoanatoxin-a are two potent cyanobacterial neurotoxins. We recently reported the identification of the gene cluster responsible for the biosynthesis of these toxins in cyanobacteria and proposed a biosynthetic scheme starting from L-proline and involving three polyketide synthases for
Phaneeswara-Rao Kommoju et al.
Biochemistry, 48(40), 9542-9555 (2009-08-26)
NikD is a flavoprotein oxidase that catalyzes the oxidation of piperideine-2-carboxylate (P2C) to picolinate in a remarkable aromatization reaction comprising two redox cycles and at least one isomerization step. Tyr258 forms part of an "aromatic cage" that surrounds the ring

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