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Key Documents

862126

Sigma-Aldrich

3,4-Dehydro-DL-proline

98%

Synonym(s):

(±)-2,5-Dihydro-1H-pyrrole-2-carboxylic acid, (±)-3-Pyrroline-2-carboxylic acid

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About This Item

Empirical Formula (Hill Notation):
C5H7NO2
CAS Number:
Molecular Weight:
113.11
Beilstein:
471693
EC Number:
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

98%

form

crystals

reaction suitability

reaction type: solution phase peptide synthesis

mp

245 °C (dec.) (lit.)

application(s)

peptide synthesis

SMILES string

OC(=O)C1NCC=C1

InChI

1S/C5H7NO2/c7-5(8)4-2-1-3-6-4/h1-2,4,6H,3H2,(H,7,8)

InChI key

OMGHIGVFLOPEHJ-UHFFFAOYSA-N

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Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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J B Cooper et al.
Plant physiology, 104(2), 747-752 (1994-02-01)
We investigated the function of cell wall hydroxyproline-rich glycoproteins by observing the effects of a selective inhibitor of prolyl hydroxylase, 3,4-dehydro-L-proline (Dhp), on wall regeneration by Nicotiana tabacum mesophyll cell protoplasts. Protoplasts treated with micromolar concentrations of Dhp do not
T A Sullivan et al.
The Journal of biological chemistry, 269(36), 22500-22506 (1994-09-09)
During development and fracture repair, endochondral bone formation is preceded by an orderly process of chondrocyte hypertrophy and cartilage matrix calcification. Analysis of calcifying versus noncalcifying cartilage has identified several differences in matrix proteins; among these are appearance of a
Ariel L L Garcia et al.
The Journal of organic chemistry, 70(3), 1050-1053 (2005-01-29)
We report herein a new, practical, and economic synthesis of the phosphodiesterase inhibitor Rolipram on a multigram scale as well as the synthesis of new 4-aryl pyrrolidones and beta-aryl-gamma-amino butyric acids (GABA derivatives) employing an efficient Heck-Matsuda arylation of 3-pyrroline
N S Fedarko et al.
Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research, 10(11), 1705-1712 (1995-11-01)
Clinical studies indicate that as a group, osteogenesis imperfecta (OI) subjects are shorter than age- and sex-matched controls. Not only somatic growth, but also cellular growth appears to be impaired, and these may be related to defects in extracellular matrix
D M Goli et al.
Carbohydrate research, 259(2), 219-241 (1994-06-17)
(2R,3R,4S)-2-Hydroxymethylpyrrolidine-3,4-diol (1,4-dideoxy-1,4-imino-D-ribitol) was synthesized in five steps from N-protected (2S)-3,4-dehydroproline methyl esters. The stereoselective reaction of osmium tetraoxide with dehydroproline derivatives gave high yields of (2S,3R,4S)-3,4-dihydroxyprolines (2,3-trans-3,4-cis-3,4-dihydroxy-L-prolines) accompanied by small amounts (< 15%) of the diastereomeric (2S,3S,4R)-3,4-dihydroxyprolines (2,3-cis-3,4-cis-3,4-dihydroxy-L-prolines). The mixture

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