35899-43-5

Basic information

• Product Name: Boc-L-Histidine(Tosyl)
• Synonyms: BOC-N-IM-4-TOLUENESYLFONYL-L-HISTIDINE;BOC-L-HISTIDINE(TOSYL);BOC-L-HIS(TOS);BOC-L-HIS(TOS)-OH;BOC-HIS(TOS);BOC-HISTIDINE(TOS)-OH;BOC-HIS(TOS)-OH;BOC-HIS(TOS)-OH IPA
• CAS NO: 35899-43-5
• Molecular Formula: C₁₈H₂₃N₃O₆S
• Molecular Weight: 409.46
• Product Categories: chiral;Amino Acid Derivatives;Amino Acids;Histidine [His, H];Boc-Amino Acids and Derivative;Amino Acids (N-Protected);Biochemistry;Boc-Amino Acids;Boc-Amino acid series
• Mol File: 35899-43-5.mol
• Article Data: 4

Chemical Properties

• Melting Point: ~125 °C (dec.)
• Appearance: White to light yellow crystal powder
• Density: 1.19
• Refractive Index: 1.594
• Storage Temp.: −20°C
• PKA: 3.50±0.10(Predicted)
• BRN: 769957
• CAS DataBase Reference: Boc-L-Histidine(Tosyl)(CAS DataBase Reference)
• NIST Chemistry Reference: Boc-L-Histidine(Tosyl)(35899-43-5)
• EPA Substance Registry System: Boc-L-Histidine(Tosyl)(35899-43-5)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 35899-43-5(Hazardous Substances Data)

Usage

Chemical Properties

White to light yellow crystal powde

Uses

Boc-L-His(Tos)-OH, is an amino acid building block used in peptide synthesis. With a growing peptide drug market the fast, reliable synthesis of peptides is of great importance.

InChI:InChI=1/C18H23N3O6S/c1-12-5-7-14(8-6-12)28(25,26)21-10-13(19-11-21)9-15(16(22)23)20-17(24)27-18(2,3)4/h5-8,10-11,15H,9H2,1-4H3,(H,20,24)(H,22,23)/t15-/m1/s1

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 17791-52-5 N-(tert-butoxycarbonyl)-L-histidine 

Downstream Products

• 55033-54-0 N-Boc-N^im-tosylhistidylglycine benzyl ester 

Relevant articles and documents

Activated ketone based inhibitors of human renin

Application of the concept of activated ketones to the design of novel and potent transition-state analog inhibitors of the aspartyl protease renin is described. Three different classes of peptidic activated ketones were synthesized: 1,1,1-trifluoromethyl ketones, α-keto esters, and α-diketones. The corresponding alcohols were also evaluated as renin inhibitors in each series. While the trifluoromethyl alcohol 12 (I50 = 4000 nM) was equipotent to the simple methyl alcohol 7 (I50 = 3200 nM), the structurally similar α-hydroxy esters (32 and 30, I50's = 5.3 and 4.7 nM, respectively) and α- hydroxy ketones (41 and 42, I50 = 23 and 15 nM, respectively) were 150- 300-fold more active. The hydrating capability of the activated ketone functionality was important for intrinsic potency in the case of trifluoromethyl ketones, as illustrated by the significantly better activity of trifluoromethyl ketone 13 (I50 = 250 nM) compared to its alcohol analog 12 (I50 = 4000 nM). It was however unimportant for the α-keto ester (20 and 31, I50 = 15 and 4.1 nM, respectively) and α-diketone (43 and 44, I50 = 52 and 28 nM, respectively) based inhibitors, since their activity was essentially similar to that of the corresponding alcohols. These results collectively suggest that, whereas the trifluoromethyl ketones derive their renin inhibitory potency primarily from their ability to become hydrated, this is not a critical feature for the activity of α-dicarbonyl-based inhibitors. The α-keto ester and α-diketone based renin inhibitors benefit predominantly from the hydrophobic and/or H-bonding type binding interactions of the neighboring ester or acyl group itself, rather than the ability of this group to deactivate the adjacent ketone group and thereby make it susceptible to hydration.

Polypeptides related to somatostatin

Compounds of the formula: STR1 wherein: X is H, Ala-Gly, Gly-Gly-Gly, Ala-D-Ala, acetyl, or benzoyl; X1 is Arg or His; X2 is Glu or Asp; X3 is Trp or D-Trp; or 6-F-D-Trp; and X4 is Cys- or D-Cys; or a non-toxic pharmaceutically acceptable acid addition salt thereof; inhibit the secretion of growth hormone and glucagon without materially affecting the secretion of insulin.