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Merck
CN

H54409

trans-4-Hydroxy-L-proline

≥99%, for peptide synthesis

Synonym(s):

(2S,4R)-4-Hydroxypyrrolidine-2-carboxylic acid, Hyp

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About This Item

Empirical Formula (Hill Notation):
C5H9NO3
CAS Number:
51-35-4
Molecular Weight:
131.13
NACRES:
NA.22
PubChem Substance ID:
24895692
UNSPSC Code:
12352209
EC Number:
200-091-9
MDL number:
MFCD00064320
Beilstein/REAXYS Number:
81441

Key Documents

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Product Name

trans-4-Hydroxy-L-proline, ≥99%

InChI key

PMMYEEVYMWASQN-DMTCNVIQSA-N

InChI

1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4+/m1/s1

SMILES string

O[C@H]1CN[C@@H](C1)C(O)=O

assay

≥99%

form

crystalline powder

optical activity

[α]25/D −75.6°, c = 1 in H2O

reaction suitability

reaction type: solution phase peptide synthesis

color

white to off-white

mp

273 °C (dec.) (lit.)

application(s)

peptide synthesis

Quality Level

200

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Application

Versatile reagent for the synthesis of neuroexcitatory kainoids and antifungal echinocandins. Also employed in the synthesis of chiral ligands for enantioselective ethylation of aldehydes.

General description

Trans-4-hydroxy-L-proline is an isomer of hydroxyproline used as a chiral building block in the production of many pharmaceuticals like neuroexcitatory kainoids.

Other Notes

Natural constituent of animal structural proteins such as collagen and elastin.

Storage Class

11 - Combustible Solids

wgk

WGK 1

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ7422
MKCZ3403
MKCZ0586
MKCX7376
0000191489

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Tetrahedron, 49, 6195-6195 (1993)
Synthetic Communications, 23, 2691-2691 (1993)
Biosynthesis of trans-4-hydroxyproline by recombinant strains of Corynebacterium glutamicum and Escherichia coli
Yi Y, et al.
BMC biotechnology, 14, 1-8 (2014)
Tetrahedron Letters, 35, 6163-6163 (1994)
Stefan de Vries et al.
Tissue engineering. Part A, 25(11-12), 830-841 (2018-05-10)
Notochordal cells (NCs) reside in the core of the healthy disc and produce soluble factors that can stimulate nucleus pulposus cells (NPCs). These NC-derived factors may be applied in intervertebral disc regeneration for treatment of low-back pain. However, identification of
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