NSC - amino acid - HYUNDAI PHARM. IND., CO., LTD.

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HYUNDAI PHARM. IND., CO., LTD.
[Korea]

Address:
213, Sosabon-1-Dong, Sosa-Gu, Bucheon 422-231, Korea Sosa-Gu Bucheon 422-231 Korea

Phone:
82-32-3479080

Contact name:
. , .

pharmaceutical

	NSC - amino acid

NSC

New Base-Labile Nsc-Amino Acids for Solid Phase Peptide Synthesis

N^α -2-(4-Nitrophenylsulfonyl) ethyloxycarbonyl)-amino acids

N^α protected amino acids for peptide synthesis are widely investigated because of their usefullness in the preparation of biologically active peptides. N^α-9-fluorenylmethoxycarbonyl (Fmoc)-amino acids have been most popular for this purpose. However, the extreme base sensitivity of Fmoc group and its instability in neutral aprotic solvents were the major weak points for peptide synthesis, Because of this, special care should be taken when it is used for the synthesis of peptides exceeding 30 residues in length.
We proved that N^α-2-(4-nitrophenylsuIfonyl)ethoxycarbonyl(Nsc)-group could be used as an alternative to Fmoc-group in peptide synthesis. Nsc-amino acids are already world-patented and routinely used in lab. for pharmaceutical peptide synthesis.

Superiority of Nsc-amino acids

Better coupling efficiency in normal condition
More stable in neutral and weakly basic media
Lower tendency to polymerize
More economic

Nsc-Amino acids and Resin Bounded Nsc-Amino acids

PRODUCT NO	PRODUCT	MORECULAR FORMULA	MW	QUANTITY
HDNS1001	N^α-Nsc-L-alanine	？C₁₂H₁₄N₂O₈S	346.32	5g	25g
HDNS1002	N^α-Nsc-L-glycine	？C₁₁H₁₂N₂O₈S	332.30	5g	25g
HDNS1003	N^α-Nsc-L-leucine	？C₁₅H₂₀N₂O₈S	388.41	5g	25g
HDNS1004	N^α-Nsc-L-isoleucine	？C₁₅H₂₀N₂O₈S	388.41	5g	25g
HDNS1005	N^α-Nsc-L-methionine	？C₁₄H₁₈N₂O₈S₂	406.44	5g	25g
HDNS1006	N^α-Nsc-L-valine	？C₁₄H₁₈N₂O₈S？	374.38	5g	25g
HDNS1007	N^α-Nsc-L-phenylalanine	？C₁₈H₁₈N₂O₈S₂	422.43	5g	25g
HDNS1008	N^α-Nsc-L-proline	？C₁₄H₁₆N₂O₈S₂	372.36	5g	25g
HDNS1009	N^α-Nsc-L-tryptophan	？C₂₀H₁₉N₃O₈S	461.46	5g	25g
HDNS1010	N^α-Nsc-S-trityl-L-cysteine	？C₃₁H₂₈N₂O₈S？	620.72	5g	25g
HDNS1011	N^α-Nsc-N^im-trityl-L-histidine	？C₃₄H₃₀N₄O₈S？	654.72	5g	25g
HDNS1012	N^α-Nsc-N^β-trityl-L-asparagine	？C₃₂H₂₉N₃O₉S？	631.69	5g	25g
HDNS1013	N^α-Nsc-N^γ-trityl-L-glutamine	？C₃₃H₃₁N₃O₉S？	645.69	5g	25g
HDNS1014	N^α-Nsc-O-t-butyl-L-serine	？C₁₆H₂₂N₂O₉S？？	418.44	5g	25g
HDNS1015	N^α-Nsc-O-t-butyl-L-threonine	？C₁₇H₂₄N₂O₉S？？	432.47	5g	25g
HDNS1016	N^α-Nsc-O-t-butyl-L-tyrosine	？C₂₂H₂₆N₂O₉S？？	494.54	5g	25g
HDNS1017	N^α-Nsc-L-aspartic acid-β-t-butyl ester	？C₁₇H₂₂N₂O₉S？？	446.45	5g	25g
HDNS1018	N^α-Nsc-L-aspartic acid-γ-t-butyl ester	？C₁₈H₂₄N₂O₁₀S？？？？？	460.48	5g	25g
HDNS1019	N^α-Nsc-N^ε-t-butoxycarbonyl-L-lusine	？C₂₀H₂₉N₃O₁₀S？？？	503.55	5g	25g
HDNS1020	N^α-Nsc-N^G-2,2,4,6,7-pentamethyladihydrobenzofuranyl -L-arginine	？C₂₈H₃₇N₅O₁₁S₂？	638.80	5g	25g
HDNS3001	Nsc-Amino acid-PAC-PEG-PS	？	？	5g	25g
HDNS4001	Nsc-Amino acid-Wang	？	？	5g	25g
HDNS5001	Nsc-Amino acid Kit (20Kinds)	？	？	1g each？	？

Comparison of Nsc-A.a and Fmoc-A.a

Properties

Nsc

Fmoc

Stability

+++

++

Inter-changeable

+++

++

addaptation to Amino acids

+++

+++

Automatic synthesis

+++

+++

Economic

+++

+

Chemical properties comparison of Fmoc and Nsc

？

Fmoc

Nsc

Cleavage rate, t _1/2

pip/ DMF (1:2)
1% DBU/20% Pip/DMF？

10-15 s
-？

90-110 s
12-15 s？

Decomposition in DMF solution

1 week
3 weeks？

10%
40%？

<1%
2%？

Vinyly-Piperidine adduct formation？

Fast/Reversible？

Very fast/Irreversible？

Polymer formation during Deprotecting？

Yes？

a little？

Available UV Range？

280-320 nm？

250-350 nm？

Application of NSC-Amino acid in SPPS(Solid-phase Peptide Synthesis)

Peptide

Active/Use

Residue

Yield(%)

Other

Fmoc

NSC

ACP

Acyl carrier protein(65-74)

10

75

78

？

INF α2

Interferon alpha 2 (130-137)

8

77

79

？

ACTH

Biologically active peptide

24

67

64

？

Salmon calcitonin

Osteophorosis(salcatonin)

32

17

16

？

LH-RH

Biologically active peptide

10

70

90

？

(D-Trp ^σ)LH-RH

Triptorelin, Biologically active peptide

10

85

90

？

AFP epitopes

Diagnostic

18-23

8 Kind

HBs

Hepatitis B virus Check

20-23

6 Kind

Peptide Libraries

Combinatorial library

6mer-8mer

Amyloid β-Protein Fragment

Alzhymer disease

11mer

Big-endotherin

？Biologically active peptide

32mer/2Cys-bridge

Substance-P

？？Biologically active peptide

12mer